ChemWiki - User contributions [en]

It:Scopolamine

2006-10-27T14:45:54Z

Eal04:

'''''Scopolamine'''''

'''Abstract'''

As is common knowledge, scopolamine (systematic name (alpha)-(hydroxymethyl) benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo [3.3.1.0 2,4] non-7-yl ester) was used during the Second World War as a 'truth drug' by the German Military and Intelligence (as many viewers and fans of 'The Guns of Navarone' would know). However, serving in this role, its success was limited, and scopolamine had (and indeed has) several other roles, neurological and otherwise, in human physiology and pharmacology. While it was used as a depressant (being an anticholigenic drug), it worked to mollify patients thanks to its sedative capabilities, thus making it easier to obtain 'blind' answers to question.

However, scopolamine is one of the drugs that is not technically synthesized chemically. Like insulin, scopolamine is produced (if required to be on a mass scale) by splicing the relevant gene responsible for its (enzyme) production onto the RNA sequence of a bacterium, usually of the ''E. coli'' family, or a derivative of it. Also, even then it needs the precursor to it to be present or produced: hyoscyamine.

In actuality, scopolamine is not all that common in the higher plants, one of the few plants capable of making it being ''Hyoscyamus niger''. In the case of ''H. niger'' the drug is produced in the branch roots. The reason behind the lack of frequency of the presence of scopolamine throughout the Solonaceae family of plants, is the lack of a particular gene. This gene is responsible for the production of the enzyme which catalyses the synthesis of scopolamine from hyoscyamine: hyoscyamine 6 [beta]-hydroxylase (often abbreviated to H6H).

Medically speaking though, the drug is rarely taken as its naturally occurring form. As with the majority of other drugs, it is taken as a salt analogue: scopolamine hydrochloride; or -methyl nitrate. Moreover, there are other analogues of scopolamine, such as atropine, though it is considered that the former has a greater central nervous systemic effect (hence its use in the treatment of motion sickness).

'''Chemical Structure & Properties'''

Scopolamine has the structure as below:

[[Image:Scopolamine.gif|thumb|left|Chemical Structure of Scopolamine]]

{| border="1"

| {{chembox header}} | Chemical & Biological Properties
|-
| colspan="1" | Chemical Formula
| colspan="2" | C17H21NO4
|-
| colspan="1" | Melting Point
| colspan="2" | 381.2-390.2°C (as nitrate), 55°C (as hydrobromide trihydrate)
|-
| colspan="1" | Principle Indications
| colspan="2" | excessive salivation, IBS, motion sickness
|-
| colspan="1" | Additional
| colspan="2" | colicky abdominal pain, sialorrhoea
|-
| colspan="1" | Mechanism
| colspan="2" | interference of ACh* in nerve impulses
|-
| colspan="1" | Biological Half-Life
| colspan="2" | approx. 9.5 hours in normal adult
|-
| colspan="1" | Solubility
| colspan="2" | highly soluble in both organic & inorganic solvents

|}
* ACh = acetylcholine, see below

[[Image:ACh.gif|thumb|left|Chemical Structure of Acetylcholine - ACh]]

'''''Biological Mechanism'''''

Scopolamine works by interfering with one of two sets of acetylcholine receptor sites which are the nicotinic (nAChR) and muscarinic (mAChR). The drug prevents the acetylcholine from binding with the latter (and nicotine induces a hypersensitivity at the former). This Is done by the scopolamine itself binding to the receptor in the place of the ACh, thereby blocking it. Having done so, being attached, it creates no inducive effect for the nerve impulse to proceed, hence, the sedative effect, as chemical signals back and forth between brain and skeletal muscles are slowed down and/or prevented. As it acts more centrally to the spinal column and brain, it therefore dulls pain to the thorax and abdomen (the nerve arcs to the vital organs and those in close proximity being much shorter), thus its effectiveness in treating motion sickness and IBS (irritable bowel syndrome).

'''References'''

Extended thanks to the following locations and parties for the use of their material:

[http://www.plantphysiol.org/cgi/content/abstract/105/2/483 Species-Dependent Expression of the H6H Gene in the Pericycle] Plant Physiology (Vol 105, 483-490): Molecular Biology & Gene Regulation - T. Kanegae, H. Kajiya, Y. Amano, T. Hashimoto and Y. Yamada

[http://redpoll.pharmacy.ualberta.ca/drugbank/cgi-bin/getCard.cgi?CARD=APRD00616.txt Scopolamine(APRD00616)] DrugBank

[http://www.drugs.com/pdr/scopolamine.html Scopolamine Drug Information] Drug Information Online (Prescription Drug Information for Consumers & Professionals)

also see [http://en.wikipedia.org/wiki/Acetylcholine Wikipedia's Acetylcholine]

It:Scopolamine

2006-10-27T12:15:29Z

Eal04:

'''''Scopolamine'''''

'''Abstract'''

As is common knowledge, scopolamine (systematic name (alpha)-(hydroxymethyl) benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo [3.3.1.0 2,4] non-7-yl ester) was used during the Second World War as a 'truth drug' by the German Military and Intelligence (as many viewers and fans of 'The Guns of Navarone' would know). However, serving in this role, its success was limited, and scopolamine had (and indeed has) several other roles, neurological and otherwise, in human physiology and pharmacology. While it was used as a depressant (being an anticholigenic drug), it worked to mollify patients thanks to its sedative capabilities, thus making it easier to obtain 'blind' answers to question.

However, scopolamine is one of the drugs that is not technically synthesized chemically. Like insulin, scopolamine is produced (if required to be on a mass scale) by splicing the relevant gene responsible for its (enzyme) production onto the RNA sequence of a bacterium, usually of the ''E. coli'' family, or a derivative of it. Also, even then it needs the precursor to it to be present or produced: hyoscyamine.

In actuality, scopolamine is not all that common in the higher plants, one of the few plants capable of making it being ''Hyoscyamus niger''. In the case of ''H. niger'' the drug is produced in the branch roots. The reason behind the lack of frequency of the presence of scopolamine throughout the Solonaceae family of plants, is the lack of a particular gene. This gene is responsible for the production of the enzyme which catalyses the synthesis of scopolamine from hyoscyamine: hyoscyamine 6 [beta]-hydroxylase (often abbreviated to H6H).

Medically speaking though, the drug is rarely taken as its naturally occurring form. As with the majority of other drugs, it is taken as a salt analogue: scopolamine hydrochloride; or -methyl nitrate. Moreover, there are other analogues of scopolamine, such as atropine, though it is considered that the former has a greater central nervous systemic effect (hence its use in the treatment of motion sickness).

'''Chemical Structure & Properties'''

Scopolamine has the structure as below:

[[Image:Scopolamine.gif|thumb|left|Chemical Structure of Scopolamine]]

{| border="1"

| {{chembox header}} | Chemical & Biological Properties
|-
| colspan="1" | Chemical Formula
| colspan="2" | C17H21NO4
|-
| colspan="1" | Melting Point
| colspan="2" | 381.2-390.2°C (as nitrate), 55°C (as hydrobromide trihydrate)
|-
| colspan="1" | Principle Indications
| colspan="2" | excessive salivation, IBS, motion sickness
|-
| colspan="1" | Additional
| colspan="2" | colicky abdominal pain, sialorrhoea
|-
| colspan="1" | Mechanism
| colspan="2" | interference of ACh* in nerve impulses
|-
| colspan="1" | Biological Half-Life
| colspan="2" | approx. 9.5 hours in normal adult
|-
| colspan="1" | Solubility
| colspan="2" | highly soluble in both organic & inorganic solvents

|}
* ACh = acetylcholine, see below

[[Image:ACh.gif|thumb|left|Chemical Structure of Acetylcholine - ACh]]

'''''Biological Mechanism'''''

Scopolamine works by interfering with one of two sets of acetylcholine receptor sites which are the nicotinic (nAChR) and muscarinic (mAChR). The drug prevents the acetylcholine from binding with the latter (and nicotine induces a hypersensitivity at the former). This Is done by the scopolamine itself binding to the receptor in the place of the ACh, thereby blocking it. Having done so, being attached, it creates no inducive effect for the nerve impulse to proceed, hence, the sedative effect, as chemical signals back and forth between brain and skeletal muscles are slowed down and/or prevented. As it acts more centrally to the spinal column and brain, it therefore dulls pain to the thorax and abdomen, thus its effectiveness in treating motion sickness and IBS (irritable bowel syndrome).

'''References'''

Extended thanks to the following locations and parties for the use of their material:

[http://www.plantphysiol.org/cgi/content/abstract/105/2/483 Species-Dependent Expression of the H6H Gene in the Pericycle] Plant Physiology (Vol 105, 483-490): Molecular Biology & Gene Regulation - T. Kanegae, H. Kajiya, Y. Amano, T. Hashimoto and Y. Yamada

[http://redpoll.pharmacy.ualberta.ca/drugbank/cgi-bin/getCard.cgi?CARD=APRD00616.txt Scopolamine(APRD00616)] DrugBank

[http://www.drugs.com/pdr/scopolamine.html Scopolamine Drug Information] Drug Information Online (Prescription Drug Information for Consumers & Professionals)

also see [http://en.wikipedia.org/wiki/Acetylcholine Wikipedia's Acetylcholine]

It:Scopolamine

2006-10-27T12:15:00Z

Eal04:

'''''Scopolamine'''''

'''Abstract'''

As is common knowledge, scopolamine (systematic name (alpha)-(hydroxymethyl) benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo [3.3.1.0 2,4] non-7-yl ester) was used during the Second World War as a 'truth drug' by the German Military and Intelligence (as many viewers and fans of 'The Guns of Navarone' would know). However, serving in this role, its success was limited, and scopolamine had (and indeed has) several other roles, neurological and otherwise, in human physiology and pharmacology. While it was used as a depressant (being an anticholigenic drug), it worked to mollify patients thanks to its sedative capabilities, thus making it easier to obtain 'blind' answers to question.

However, scopolamine is one of the drugs that is not technically synthesized chemically. Like insulin, scopolamine is produced (if required to be on a mass scale) by splicing the relevant gene responsible for its (enzyme) production onto the RNA sequence of a bacterium, usually of the ''E. coli'' family, or a derivative of it. Also, even then it needs the precursor to it to be produced: hyoscyamine.

In actuality, scopolamine is not all that common in the higher plants, one of the few plants capable of making it being ''Hyoscyamus niger''. In the case of ''H. niger'' the drug is produced in the branch roots. The reason behind the lack of frequency of the presence of scopolamine throughout the Solonaceae family of plants, is the lack of a particular gene. This gene is responsible for the production of the enzyme which catalyses the synthesis of scopolamine from hyoscyamine: hyoscyamine 6 [beta]-hydroxylase (often abbreviated to H6H).

Medically speaking though, the drug is rarely taken as its naturally occurring form. As with the majority of other drugs, it is taken as a salt analogue: scopolamine hydrochloride; or -methyl nitrate. Moreover, there are other analogues of scopolamine, such as atropine, though it is considered that the former has a greater central nervous systemic effect (hence its use in the treatment of motion sickness).

'''Chemical Structure & Properties'''

Scopolamine has the structure as below:

[[Image:Scopolamine.gif|thumb|left|Chemical Structure of Scopolamine]]

{| border="1"

| {{chembox header}} | Chemical & Biological Properties
|-
| colspan="1" | Chemical Formula
| colspan="2" | C17H21NO4
|-
| colspan="1" | Melting Point
| colspan="2" | 381.2-390.2°C (as nitrate), 55°C (as hydrobromide trihydrate)
|-
| colspan="1" | Principle Indications
| colspan="2" | excessive salivation, IBS, motion sickness
|-
| colspan="1" | Additional
| colspan="2" | colicky abdominal pain, sialorrhoea
|-
| colspan="1" | Mechanism
| colspan="2" | interference of ACh* in nerve impulses
|-
| colspan="1" | Biological Half-Life
| colspan="2" | approx. 9.5 hours in normal adult
|-
| colspan="1" | Solubility
| colspan="2" | highly soluble in both organic & inorganic solvents

|}
* ACh = acetylcholine, see below

[[Image:ACh.gif|thumb|left|Chemical Structure of Acetylcholine - ACh]]

'''''Biological Mechanism'''''

Scopolamine works by interfering with one of two sets of acetylcholine receptor sites which are the nicotinic (nAChR) and muscarinic (mAChR). The drug prevents the acetylcholine from binding with the latter (and nicotine induces a hypersensitivity at the former). This Is done by the scopolamine itself binding to the receptor in the place of the ACh, thereby blocking it. Having done so, being attached, it creates no inducive effect for the nerve impulse to proceed, hence, the sedative effect, as chemical signals back and forth between brain and skeletal muscles are slowed down and/or prevented. As it acts more centrally to the spinal column and brain, it therefore dulls pain to the thorax and abdomen, thus its effectiveness in treating motion sickness and IBS (irritable bowel syndrome).

'''References'''

Extended thanks to the following locations and parties for the use of their material:

[http://www.plantphysiol.org/cgi/content/abstract/105/2/483 Species-Dependent Expression of the H6H Gene in the Pericycle] Plant Physiology (Vol 105, 483-490): Molecular Biology & Gene Regulation - T. Kanegae, H. Kajiya, Y. Amano, T. Hashimoto and Y. Yamada

[http://redpoll.pharmacy.ualberta.ca/drugbank/cgi-bin/getCard.cgi?CARD=APRD00616.txt Scopolamine(APRD00616)] DrugBank

[http://www.drugs.com/pdr/scopolamine.html Scopolamine Drug Information] Drug Information Online (Prescription Drug Information for Consumers & Professionals)

also see [http://en.wikipedia.org/wiki/Acetylcholine Wikipedia's Acetylcholine]

File:ACh.gif

2006-10-27T12:06:28Z

Eal04:

It:Scopolamine

2006-10-27T11:44:01Z

Eal04:

'''''Scopolamine'''''

'''Abstract'''

As is common knowledge, scopolamine (systematic name (alpha)-(hydroxymethyl) benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo [3.3.1.0 2,4] non-7-yl ester) was used during the Second World War as a 'truth drug' by the German Military and Intelligence (as many viewers and fans of 'The Guns of Navarone' would know). However, serving in this role, its success was limited, and scopolamine had (and indeed has) several other roles, neurological and otherwise, in human physiology and pharmacology. While it was used as a depressant (being an anticholigenic drug), it worked to mollify patients thanks to its sedative capabilities, thus making it easier to obtain 'blind' answers to question.

However, scopolamine is one of the drugs that is not technically synthesized chemically. Like insulin, scopolamine is produced (if required to be on a mass scale) by splicing the relevant gene responsible for its (enzyme) production onto the RNA sequence of a bacterium, usually of the ''E. coli'' family, or a derivative of it. Also, even then it needs the precursor to it to be produced: hyoscyamine.

In actuality, scopolamine is not all that common in the higher plants, one of the few plants capable of making it being ''Hyoscyamus niger''. In the case of ''H. niger'' the drug is produced in the branch roots. The reason behind the lack of frequency of the presence of scopolamine throughout the Solonaceae family of plants, is the lack of a particular gene. This gene is responsible for the production of the enzyme which catalyses the synthesis of scopolamine from hyoscyamine: hyoscyamine 6 [beta]-hydroxylase (often abbreviated to H6H).

Medically speaking though, the drug is rarely taken as its naturally occurring form. As with the majority of other drugs, it is taken as a salt analogue: scopolamine hydrochloride; or -methyl nitrate.

'''Chemical Structure & Properties'''

Scopolamine has the structure as below:

[[Image:Scopolamine.gif|thumb|left|Chemical Structure of Scopolamine]]

{| border="1"

| {{chembox header}} | Chemical & Biological Properties
|-
| colspan="1" | Chemical Formula
| colspan="2" | C17H21NO4
|-
| colspan="1" | Melting Point
| colspan="2" | 381.2-390.2°C (as nitrate), 55°C (as hydrobromide trihydrate)
|-
| colspan="1" | Principle Indications
| colspan="2" | excessive salivation, IBS, motion sickness
|-
| colspan="1" | Additional
| colspan="2" | colicky abdominal pain, sialorrhoea
|-
| colspan="1" | Mechanism
| colspan="2" | interference of ACh in nerve impulses
|-
| colspan="1" | Biological Half-Life
| colspan="2" | approx. 9.5 in normal adult
|-
| colspan="1" | Solubility
| colspan="2" | highly soluble in both organic & inorganic solvents

|}

'''References'''

Extended thanks to the following locations and parties for the use of their material:

[http://www.plantphysiol.org/cgi/content/abstract/105/2/483 Species-Dependent Expression of the H6H Gene in the Pericycle] Plant Physiology (Vol 105, 483-490): Molecular Biology & Gene Regulation - T. Kanegae, H. Kajiya, Y. Amano, T. Hashimoto and Y. Yamada

[http://redpoll.pharmacy.ualberta.ca/drugbank/cgi-bin/getCard.cgi?CARD=APRD00616.txt Scopolamine(APRD00616)] DrugBank

[http://www.drugs.com/pdr/scopolamine.html Scopolamine Drug Information] Drug Information Online (Prescription Drug Information for Consumers & Professionals)

File:Scopolamine.gif

2006-10-27T10:34:57Z

Eal04:

It:projects

2006-10-27T10:26:19Z

Eal04: /* Supplemental Project Page */

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Further Abstract

2006-10-24T13:44:25Z

Eal04:

'''''Piperine: a Further Study'''''

'''History & Background'''

Piperine is the active (contributor to the taste) of both black and white pepper, but has a different effect in each case, due to the timing whereby each is extracted. Black pepper is taken from the unripe green berries of the vine (and then sun-dried), whereas the white pepper is taken from the ripe red berries, hence the much milder taste of the white.

'''Abstract'''

It is widely known that pepper leaves a severe burning sensation on the tongue when it is ingested. However, what is not picked up on is that the burning only after a few moments that it has been in contact with the tongue. Several other foodstuffs (and their chemical constituents) can be effected and thus tasted very promptly. The reason for the delayed action of the pepper is the nature of the piperine, that which gives it its 'fire'. Solid state piperine is not particuarly reactive at all, which is why it is essentially tasteless at first. However, upon solvation (namely in one's saliva) its reactivity increases greatly. The reasoning behind the strong reactivity of aqueous (or other solvated forms) of piperine comes in the form of its nature as a greatly unsaturated compound.

''References''

Extended thanks to the following locations and parties for the use of their material:

[http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm ''Piper nigrum'' Piperine: History & Characteristics] Piperin Home Page (& subsidiaries)

[http://unitproj1.library.ucla.edu/biomed/spice/index.cfm?displayID=20 Piperine & Other Medicinal Spices & Their Effects] The University of California: Los Angeles, History and Special Collections: the Louise M. Darling Biomedical Library (Online)

Further Abstract

2006-10-24T13:24:02Z

Eal04:

'''''Piperine: a Further Study'''''

'''History & Background'''

It is widely known that pepper leaves a severe burning sensation on the tongue when it is ingested. However, what is not picked up on is that the burning only after a few moments that it has been in contact with the tongue. Several other foodstuffs (and their chemical constituents) can be effected and thus tasted very promptly. The reason for the delayed action of the pepper is the nature of the piperine, that which gives it its 'fire'. Solid state piperine is not particuarly reactive at all, which is why it is essentially tasteless at first. However, upon solvation (namely in one's saliva) its reactivity increases greatly.

'''Abstract'''

The reasoning behind the strong reactivity of aqueous (or other solvated forms) of piperine comes in the form of its nature as a greatly unsaturated compound.

''References''

Extended thanks to the following locations and parties for the use of their material:

[http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm ''Piper nigrum'' Piperine: History & Characteristics] Piperin Home Page (& subsidiaries)

It:Piperine

2006-10-24T13:11:33Z

Eal04:

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Piperine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:piperine.png|Piperine]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"| 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-
2,4-pentadienyl]piperidine
|-
| colspan="1" |Auto name
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C17H19NO3
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O=C(N2CCCCC2)/C=C/C=C/C1=CC(OCO3)=C3C=C1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |285.34
|-
| colspan="1" |Appearance
| colspan="2" |Yellow/Green Powder
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |90741
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-62-2, 495-91-0, 7780-20-3, 30511-76-3, 30511-77-4
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)| Solubility in Water
| colspan="2" | 40mg/L @ 219K [http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341]
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |131-135oC
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |Decomposes
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine] 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[http://www.sigmaaldrich.com/spectra/fnmr/FNMR011260.PDF NMR]], [[Mass spectrometry|MS]], [[Isotope Distribution Pattern|IDP]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}

==Introduction==

'''Piperine''' is a substance found naturally in plants belonging to the Piperaceae family, such as Piper nigrum L, commonly known as black pepper.

Piperine can be extracted directly from black pepper by using ethanol. At first, piperine is tasteless but a burning sensation on the tongue is felt soon after ingestion.

[[Image:piperine.gif]]
<div align="left"> 
== '''Properties of Piperine''' ==
</div>
{| border="1"
|+
! Property !! Value !!
|-
! Molecular Formula
| C17H19NO3 ||
|-
! Molecular Weight
|285.34 amu ||
|-
! Melting Point
|131-135°C||
|}

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 19-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 19-Oct-06 0 NONE 4
ATOM 1 O 0 3.507 -2.115 -0.157 0.00 0.00 O+0
ATOM 2 C 0 3.446 -0.904 -0.277 0.00 0.00 C+0
ATOM 3 N 0 4.578 -0.181 -0.385 0.00 0.00 N+0
ATOM 4 C 0 4.521 1.265 -0.642 0.00 0.00 C+0
ATOM 5 C 0 5.340 1.989 0.430 0.00 0.00 C+0
ATOM 6 C 0 6.757 1.412 0.460 0.00 0.00 C+0
ATOM 7 C 0 6.697 -0.074 0.821 0.00 0.00 C+0
ATOM 8 C 0 5.893 -0.821 -0.242 0.00 0.00 C+0
ATOM 9 C 0 2.187 -0.258 -0.309 0.00 0.00 C+0
ATOM 10 C 0 1.052 -0.972 -0.096 0.00 0.00 C+0
ATOM 11 C 0 -0.203 -0.328 -0.128 0.00 0.00 C+0
ATOM 12 C 0 -1.335 -1.040 0.084 0.00 0.00 C+0
ATOM 13 C 0 -2.641 -0.370 0.051 0.00 0.00 C+0
ATOM 14 C 0 -3.813 -1.104 0.270 0.00 0.00 C+0
ATOM 15 C 0 -5.039 -0.468 0.238 0.00 0.00 C+0
ATOM 16 O 0 -6.306 -0.943 0.415 0.00 0.00 O+0
ATOM 17 C 0 -7.174 0.067 -0.133 0.00 0.00 C+0
ATOM 18 O 0 -6.418 1.283 0.009 0.00 0.00 O+0
ATOM 19 C 0 -5.108 0.903 -0.013 0.00 0.00 C+0
ATOM 20 C 0 -3.945 1.631 -0.230 0.00 0.00 C+0
ATOM 21 C 0 -2.718 1.007 -0.194 0.00 0.00 C+0
ATOM 22 H 0 4.938 1.477 -1.627 0.00 0.00 H+0
ATOM 23 H 0 3.485 1.602 -0.601 0.00 0.00 H+0
ATOM 24 H 0 5.386 3.053 0.196 0.00 0.00 H+0
ATOM 25 H 0 4.870 1.850 1.403 0.00 0.00 H+0
ATOM 26 H 0 7.218 1.530 -0.520 0.00 0.00 H+0
ATOM 27 H 0 7.350 1.943 1.206 0.00 0.00 H+0
ATOM 28 H 0 7.708 -0.479 0.865 0.00 0.00 H+0
ATOM 29 H 0 6.214 -0.194 1.790 0.00 0.00 H+0
ATOM 30 H 0 5.763 -1.860 0.061 0.00 0.00 H+0
ATOM 31 H 0 6.419 -0.779 -1.195 0.00 0.00 H+0
ATOM 32 H 0 2.130 0.803 -0.502 0.00 0.00 H+0
ATOM 33 H 0 1.110 -2.033 0.097 0.00 0.00 H+0
ATOM 34 H 0 -0.260 0.733 -0.321 0.00 0.00 H+0
ATOM 35 H 0 -1.277 -2.101 0.277 0.00 0.00 H+0
ATOM 36 H 0 -3.759 -2.165 0.463 0.00 0.00 H+0
ATOM 37 H 0 -7.381 -0.135 -1.184 0.00 0.00 H+0
ATOM 38 H 0 -8.102 0.124 0.436 0.00 0.00 H+0
ATOM 39 H 0 -4.003 2.692 -0.423 0.00 0.00 H+0
ATOM 40 H 0 -1.817 1.577 -0.363 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 9 0 NONE 46
CONECT 3 2 8 4 0 NONE 47
CONECT 4 3 5 22 23 NONE 48
CONECT 5 4 6 24 25 NONE 49
CONECT 6 5 7 26 27 NONE 50
CONECT 7 6 8 28 29 NONE 51
CONECT 8 7 3 30 31 NONE 52
CONECT 9 2 10 32 0 NONE 53
CONECT 10 9 11 33 0 NONE 54
CONECT 11 10 12 34 0 NONE 55
CONECT 12 11 13 35 0 NONE 56
CONECT 13 12 21 14 0 NONE 57
CONECT 14 13 15 36 0 NONE 58
CONECT 15 14 16 19 0 NONE 59
CONECT 16 15 17 0 0 NONE 60
CONECT 17 16 18 37 38 NONE 61
CONECT 18 17 19 0 0 NONE 62
CONECT 19 15 18 20 0 NONE 63
CONECT 20 19 21 39 0 NONE 64
CONECT 21 20 13 40 0 NONE 65
END NONE 66
</inlineContents>
</jmolApplet>
</jmol>

==Safety==

Piperine is a harmful substance and the dust/vapour should not be inhaled. As with most chemicals, contact with the skin and eyes should be avoided.

==External Links==

*[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine]
*[http://www.uni-bayreuth.de/departments/oc1/Publications/ref09.pdf Three-component synthesis of (''E'')-(α,β)- unsaturated amides of the piperine family]

==References==

*[http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm Piperine Home Page]
*[http://http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml Piperine]
*[http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341 National Library of Medicine, Specialised Information Services]
*[http://www.sigmaaldrich.com/Area_of_Interest/Europe_Home/UK.html Sigma-Alrich UK website]

[[Further Abstract]]

Further Abstract

2006-10-24T13:11:22Z

Eal04:

'''''Piperine: a Further Study'''''

It:Gingerone

2006-10-24T13:06:54Z

Eal04:

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |2D Structure of Zingerone
|-
| align="center" colspan="3" bgcolour="#ffffff" | [[Image:Untitled.gif]]
|-
! {{chembox header}} colspan="3" |3D structure of Zingerone <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>
HEADER NONAME 20-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Oct-06 0 NONE 4
ATOM 1 O 0 3.909 -1.039 -0.489 0.00 0.00 O+0
ATOM 2 C 0 2.599 -0.845 -0.181 0.00 0.00 C+0
ATOM 3 C 0 2.106 0.445 -0.009 0.00 0.00 C+0
ATOM 4 O 0 2.934 1.515 -0.149 0.00 0.00 O+0
ATOM 5 C 0 2.143 2.682 0.086 0.00 0.00 C+0
ATOM 6 C 0 0.770 0.636 0.305 0.00 0.00 C+0
ATOM 7 C 0 -0.070 -0.452 0.446 0.00 0.00 C+0
ATOM 8 C 0 -1.523 -0.242 0.787 0.00 0.00 C+0
ATOM 9 C 0 -2.335 -0.105 -0.502 0.00 0.00 C+0
ATOM 10 C 0 -3.788 0.105 -0.161 0.00 0.00 C+0
ATOM 11 C 0 -4.804 0.269 -1.261 0.00 0.00 C+0
ATOM 12 O 0 -4.137 0.142 0.995 0.00 0.00 O+0
ATOM 13 C 0 0.419 -1.734 0.275 0.00 0.00 C+0
ATOM 14 C 0 1.750 -1.932 -0.044 0.00 0.00 C+0
ATOM 15 H 0 4.384 -1.120 0.349 0.00 0.00 H+0
ATOM 16 H 0 1.331 2.723 -0.641 0.00 0.00 H+0
ATOM 17 H 0 1.728 2.643 1.093 0.00 0.00 H+0
ATOM 18 H 0 2.767 3.570 -0.016 0.00 0.00 H+0
ATOM 19 H 0 0.385 1.637 0.439 0.00 0.00 H+0
ATOM 20 H 0 -1.889 -1.094 1.359 0.00 0.00 H+0
ATOM 21 H 0 -1.629 0.666 1.381 0.00 0.00 H+0
ATOM 22 H 0 -1.969 0.747 -1.074 0.00 0.00 H+0
ATOM 23 H 0 -2.229 -1.013 -1.096 0.00 0.00 H+0
ATOM 24 H 0 -4.306 0.208 -2.228 0.00 0.00 H+0
ATOM 25 H 0 -5.551 -0.521 -1.186 0.00 0.00 H+0
ATOM 26 H 0 -5.291 1.240 -1.164 0.00 0.00 H+0
ATOM 27 H 0 -0.240 -2.582 0.386 0.00 0.00 H+0
ATOM 28 H 0 2.130 -2.934 -0.178 0.00 0.00 H+0
CONECT 1 2 15 0 0 NONE 33
CONECT 2 1 14 3 0 NONE 34
CONECT 3 2 4 6 0 NONE 35
CONECT 4 3 5 0 0 NONE 36
CONECT 5 4 16 17 18 NONE 37
CONECT 6 3 7 19 0 NONE 38
CONECT 7 6 8 13 0 NONE 39
CONECT 8 7 9 20 21 NONE 40
CONECT 9 8 10 22 23 NONE 41
CONECT 10 9 11 12 0 NONE 42
CONECT 11 10 24 25 26 NONE 43
CONECT 12 10 0 0 0 NONE 44
CONECT 13 7 14 27 0 NONE 45
CONECT 14 13 2 28 0 NONE 46
END NONE 47
</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | Properties
|-
| colspan="1" |IUPAC Systematic Name
| colspan="2"|4-(4-hydroxy-3-methoxyphenyl)-2-butanone
|-
| colspan="1" |Molecular formula
| colspan="2" |C11H14O3
|-
| colspan="1" |SMILES String
| colspan="2" |OC1=C(OC)C=C(CCC(C)=O)C=C1
|-
| colspan="1" |Molecular Mass
| colspan="2" |194 g/mol
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |2051099
|-
| colspan="1" |CAS Registry Number
| colspan="2" |122-48-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| Melting Point
| colspan="2" |40-42°C

|}

==Zingerone== is the molecule responsible for most of the taste of cooked ginger. It is also a week antioxidant, and this may account for some of the proposed medicinal properties of the compound.

Many other molecules which give foods taste and smell are chemically similar to zingerone, most notably capsaicin and vanillin, which give vanilla and hot peppers their tastes. Zingerone has a higher molecular weight than vanillin, and contains a carbonyl side group which allows stronger Van Der Waals interactions. This means zingerone can bind strongly to itself when compared with molecules like vanillin. This in turn makes zingerone less volatile, which accounts for the fact that while vanilla and ginger give similarly strong tastes, vanilla's smell is much more potent. It can escape more readily as a gas. On the other hand, capsaicin is a heavier molecule than zingerone, is much less volatile, and therefore is completely odourless.
To compare zingerone with several other 'taste' molecules see [http://antoine.frostburg.edu/chem/senese/101/features/capsaicin.shtml General Chemistry Online: Fire and Spice]

Fresh ginger contains no zingerone. When ginger is cooked gingerol, a molecule present in fresh ginger, reacts to give zingerone. Whereas gingerol has an extremely strong taste, zingerone has a milder, sweeter taste.

[[Image:gingerol.gif|50px]]
Chemical structure of gingerol, a precursor of gingerone

There is some evidence that gingerol has therapeutic properties that help with symptoms like nausea and vomiting, and may be of some use as a natural remedy to things like morning sickness and seasickness. There is some controversy as to these effects because not all studies show any effect when compared with a placebo.
[http://bja.oxfordjournals.org/cgi/content/abstract/84/3/367 Article:efficacy of ginger for nausea and vomiting]

'''Zingerone synthesis'''

[[Image:Zingerone synthesis.gif|thumb|Description]]

In 1968 CONNELL and SUTHERLAND examined the structures and synthesis of zingerone. They found that it was possible to synthesise zingerone by hydrolysing gingerol using hot aqueous barium hydroxide solution. Other aldehydes are also produced in this reaction.

[[Image:Gingerol hydrolysis.gif|thumb|Description]]

{|-
! {{chembox header}} colspan="3" | Properties of Gingerol
|-
| colspan="1" |CAS Registry Number
| colspan="2"|41743-68-4, 77398-90-4
|-
| colspan="1" |Chemical Name
| colspan="2" |[4]-Gingerol
|-
| colspan="1" |Autoname
| colspan="2" |5-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)-octan-3-one
|-
| colspan="1" |Molecular Formula
| colspan="2" |C15H22O4
|-
| colspan="1" |Molecular Weight
| colspan="2" |266.34
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |2051099
|-
| Melting Point
| colspan="2" |74-75°C

|}

==Spectra of Zingerone==

''Infrared Spectrum'':
[[Image:irzingerone.PNG]]

''Mass Spectrum'':
[[Image:Zingerone.jpg|thumb|Description]]

==References==
* Spectra obtained from NIST Chemistry Web book - [http://webbook.nist.gov/chemistry/]
* Connell, D. W.; Sutherland, M. D. A Re-Examination of Gingerol, Shogaol, and Zingerone, The Pungent Principles of Ginger (Zingiber Officinule Roscoe). Aust. J. Chem. 1969,22,
1033-1043, and references cited therein.

[[Further Abstract & Syntheses]]

Further Abstract & Syntheses

2006-10-24T13:02:27Z

Eal04:

'''''Abstract'''''

Zingerone takes the systematic name of (4-(4-hydroxy-3-methoxyphenyl)-2-butanone). As mentioned, it is the natural flavour that is a derivative of the even more basically occurring zingerol. There are several methods by which it can be produced, and not just by the simple process of 'cooking'. Below is a schematic of the path by which it can be synthesized by cross-aldol condensation, followed by a catalysed hydrogenation.

'''''Zingerone Alternative Synthesis'''''

[[Image:ZingeroneSynth.gif|thumb|left|Synthetic Route for Zingerone via Vanillin]]

''Derivatives''

As can be observed from the image as above, there is a methoxy group para to the hydroxy group on the phenyl ring. If this group were to be replaced by a hydrogen atom, it would be converted to rheosmin (otherwise known as the 'raspberry ketone'), another naturally occurring flavour. However, for this, the starting reagent can not, obviously, be vanillin, so instead 4-hydroxybenzaldehyde is used, which is essentially a direct analogue of the rheosmin (as zingerone is to vanillin). Further to this, small amounts of zingerone can be found in raspberries, as well as in the naturally greater amounts in ginger roots.

''Other Properties''

As would be expected, zingerone occurs as crystals that can vary in colour from dirty yellow to faded brown. Strangely, though, with its numbers of sites of electronegativity (three oxygens spaced out across the compound), one would have assumed that since the structure was more long than large that it would be in the liquid phase at room temperature. As below, we note that it is solid, but it still liquidates at a relatively low temperature. Instead, the aforementioned property affords itself to the high boiling point. However, it would be fair to note that the impedement of tail prevents the full effect of the dipoles from taking place, hence why zingerone has a boiling point that is barely higher than that of vanillin (285°C).

{| border="1"

| {{chembox header}} | Physical & Other Properties
|-
| colspan="1" | Melting Point
| colspan="2"| 40-41°C at 1 atm
|-
| colspan="1" | Boiling Point
| colspan="2" | 290°C at 1 atm
|-
| colspan="1" | Refractive Index
| colspan="2" | 1.544 at 20°C
|-
| colspan="1" | Natural Concentration
| colspan="2" | 80.00 ppm
|-
| colspan="1" | Water Solubility
| colspan="2" | Insoluble
|-
| colspan="1" | Organic Solubility
| colspan="2" | to 1.1% in ethanol

|}

''History & Background''

It would be fair to note that zingerone (''Zingiber officinale''(and thus its derivative of zingerol) is part of a set of compounds known as the vallinoids (which includes the following: vanillin (''Vanilla planifolia''); capsaicin (chile pepper: ''Capsicum annuum''); and eugenol (clove: ''Eugenia caryophyllis''). All of these compounds have the characterisation of having a specific set of receptors on sensory cells in the relevant areas of the central and peripheral nervous systems. Each compound binds to a particular receptor, thus causing a fluctuation in the level of sensory effects. Of course, each of the vallinoids has a differing (quantitative and qualitative effect). Zingerone, relatively speaking is quite neutral in its effect, though it will dull certain sweetnesses, and offers moderate change to the said senses.

'''References'''

Extended thanks to the following locations and parties for the use of their material:

[http://www.springerlink.com/content/x5166678x5j77018/?p=eb645c778df64b24967a090e04a74057&pi=6 Rheosmin (“Raspberry Ketone”) and Zingerone, and Their Preparation by Crossed Aldol-Catalytic Hydrogenation Sequences] The Chemical Educator: Chemistry & Materials Science (Vol. 1, No. 3, August 1996) Leverett R Smith

[http://unitproj1.library.ucla.edu/biomed/spice/index.cfm?displayID=27 Vanilla & Other Medicinal Spices & Their Effects] The University of California: Los Angeles, History and Special Collections: the Louise M. Darling Biomedical Library (Online)

[http://www.thegoodscentscompany.com/data/rw1006231.html Zingerone: Properties (Physical & Otherwise)] The Good Scent Company: Scents & Chemical Database

File:ZingeroneSynth.gif

2006-10-24T12:02:53Z

Eal04: Here is a schematic of a two step process by which zingerone can be produced from a condensation of acetone with vanillin.

Here is a schematic of a two step process by which zingerone can be produced from a condensation of acetone with vanillin.