{| border="1" cellpadding="2" cellspacing="0" align="right" style="margin-left:1em; background: #ffffff;"
! colspan="2" align=center bgcolor="#ccccff" | '''Limonene'''
|-
| colspan="2" align="center" |
|-
| IUPAC nomenclature|Chemical name
| 1-methyl-4-prop-1-en-2-yl-cyclohexene
|-
| Synonyms
| 4-isopropenyl-1-methylcyclohexene<br/>Racemic: DL-limonene; dipentene
|-
| Chemical formula
| C<sub>10</sub>H<sub>16
|-
| Molecular mass
| 136.24 g/mol
|-
| Melting point
| -95.2 °C
|-
| Boiling point
| 176 °C
|-
| Density
| 0.8411 g/cm<sup>3</sup>
|-
| Refractive index
| 1.4730
|-
| Flash point
| 50°C
|-
| SMILES
| CC1=CCC(C(=C)(C))CC1
|-
|-
| [http://newsearchch.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet?action=PowerSearch&query=msds._msdsID%3D4212&sort=&target=msds&from=0&realQuery=rn.value%3D%3D%225989-27-5%22&searchTemplate=rn.value%3D%3D%3F&searchValue=5989-27-5&history=off&options=brandqtyoffer&format=ccd MSDS]
|-
|}
=Limonene=
<div>
[[image:limonene.bmp]]
</div>
Limonene is an organic molecule, one enantiomer of which smells extremely like oranges (D-limonene, the (R)- enantiomer), being the active ingredient in citrus. The other enantiomer smells like something of a cross between pine and turpentine, and unsurprisingly the molecule is classed as a "turpene".

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Nov-06 0 NONE 4
ATOM 1 C 0 3.598 0.080 -0.042 0.00 0.00 C+0
ATOM 2 C 0 2.092 0.036 -0.030 0.00 0.00 C+0
ATOM 3 C 0 1.452 1.160 -0.053 0.00 0.00 C+0
ATOM 4 C 0 -0.044 1.277 -0.036 0.00 0.00 C+0
ATOM 5 C 0 -0.681 -0.063 -0.413 0.00 0.00 C+0
ATOM 6 H 0 -0.509 -0.266 -1.470 0.00 0.00 H+0
ATOM 7 C 0 -2.163 -0.013 -0.142 0.00 0.00 C+0
ATOM 8 C 0 -2.665 0.246 1.255 0.00 0.00 C+0
ATOM 9 C 0 -3.014 -0.194 -1.121 0.00 0.00 C+0
ATOM 10 C 0 -0.034 -1.164 0.436 0.00 0.00 C+0
ATOM 11 C 0 1.428 -1.310 0.001 0.00 0.00 C+0
ATOM 12 H 0 3.931 1.117 -0.069 0.00 0.00 H+0
ATOM 13 H 0 3.983 -0.402 0.858 0.00 0.00 H+0
ATOM 14 H 0 3.971 -0.445 -0.922 0.00 0.00 H+0
ATOM 15 H 0 2.030 2.072 -0.087 0.00 0.00 H+0
ATOM 16 H 0 -0.373 1.565 0.962 0.00 0.00 H+0
ATOM 17 H 0 -0.355 2.039 -0.751 0.00 0.00 H+0
ATOM 18 H 0 -2.786 1.318 1.405 0.00 0.00 H+0
ATOM 19 H 0 -3.625 -0.252 1.394 0.00 0.00 H+0
ATOM 20 H 0 -1.946 -0.143 1.977 0.00 0.00 H+0
ATOM 21 H 0 -4.076 -0.159 -0.926 0.00 0.00 H+0
ATOM 22 H 0 -2.655 -0.380 -2.122 0.00 0.00 H+0
ATOM 23 H 0 -0.081 -0.889 1.490 0.00 0.00 H+0
ATOM 24 H 0 -0.558 -2.106 0.276 0.00 0.00 H+0
ATOM 25 H 0 1.466 -1.761 -0.990 0.00 0.00 H+0
ATOM 26 H 0 1.953 -1.951 0.709 0.00 0.00 H+0
CONECT 1 2 12 13 14 NONE 31
CONECT 2 1 11 3 0 NONE 32
CONECT 3 2 4 15 0 NONE 33
CONECT 4 3 5 16 17 NONE 34
CONECT 5 4 6 7 10 NONE 35
CONECT 7 5 8 9 0 NONE 36
CONECT 8 7 18 19 20 NONE 37
CONECT 9 7 21 22 0 NONE 38
CONECT 10 5 11 23 24 NONE 39
CONECT 11 10 2 25 26 NONE 40
END NONE 41
NONE 66
</inlineContents>
</jmolApplet>
</jmol>

==Uses==

Limonene has long been used to give an orange or a lemon flavour to food products (depending on what it's used with), and also to give that lovely "lemon fresh" smell to things like fairy liquid and bleach. Recently however, it has been realised that it can be used as a solvent for cleaning products on its own, leading to an explosion in "more natural" cleaning products - Mr Muscle Orange Action is a good example.(Despite the excellent marketing point that being a "more natural" product is, the reason limonene is now being used as solvent is that it is much less hazardous to health than some things that have been used as solvents in cleaning products in the past...)

==Industrial Manufacture==

Industrially, limonene is extracted as an oil from the rinds of citrus fruits (most commonly oranges, lemons and limes) and as such is produced as a by-product of the juice industry. Two grades of limonene oil are obtained; the first, food grade oil, is extracted by pressing the fruit rinds. This oil is then purified by distillation (some of the distillates can also be recovered for sale, of use as flavourings or fragrances). After this pressing process, the peel is then steamed heated; when the steam is condensed, a layer of limonene oil is left floating on its surface. This is known as technical grade limonene, and is what is used in cleaning products.

==Sythesis==

The simplest way to synthesize limonene, and the one used industrially, is by the Diels-Alder reaction (in this case a dimerization as well) between two molecules of isoprene (this leads to its synonym, dipentene):

[[image:limonenesynth.JPG]]

However, the problem with this synthetic route is that it produces both enantiomers, leading to problems of separation and isolation. Fortunately it has been discovered that reacting isoprene with mthyl vinyl ketone, followed by a wittig reaction to convert the carbonyl group to a c=c double bond:

[[image:limonenesynth3.JPG]]

This reaction can be sped up and made more regio-slective by the addition of a lewis acidic catalyst, such as AlCl3. The product mixture is still racemic, but much less so than with the dimerization reaction; roughly 75% of the useful enantiomer instead of just under 50%.

==Spectroscopy==
===Infra red spectrum===
<div>
[[image:limoneneir.gif]]
<\div>

==References==
1. [http://www.sdbs.org The Sppectral Database System]

2. [http://en.wikipedia.org/wiki/Limonene Wikikpedia.org]

3. [http://www.scjohnson.co.uk/ S. C. Johnson wbesite (the makers of Mr Muscle Orange Action)]

4. [http://www.floridachemical.com/whatisd-limonene.htm the website of The Florida Chemical Company Ltd]

2006-11-21T11:38:24Z

Rpj05:

It:limonene

2006-11-21T11:31:40Z

Rpj05:

{| border="1" cellpadding="2" cellspacing="0" align="right" style="margin-left:1em; background: #ffffff;"
! colspan="2" align=center bgcolor="#ccccff" | '''Limonene'''
|-
| colspan="2" align="center" |
|-
| IUPAC nomenclature|Chemical name
| 1-methyl-4-prop-1-en-2-yl-cyclohexene
|-
| Synonyms
| 4-isopropenyl-1-methylcyclohexene<br/>Racemic: DL-limonene; dipentene
|-
| Chemical formula
| C<sub>10</sub>H<sub>16
|-
| Molecular mass
| 136.24 g/mol
|-
| Melting point
| -95.2 °C
|-
| Boiling point
| 176 °C
|-
| Density
| 0.8411 g/cm<sup>3</sup>
|-
| Refractive index
| 1.4730
|-
| Flash point
| 50°C
|-
| SMILES
| CC1=CCC(C(=C)(C))CC1
|-
|}
=Limonene=
<div>
[[image:limonene.bmp]]
</div>
Limonene is an organic molecule, one enantiomer of which smells extremely like oranges (D-limonene, the (R)- enantiomer), being the active ingredient in citrus. The other enantiomer smells like something of a cross between pine and turpentine, and unsurprisingly the molecule is classed as a "turpene".

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Nov-06 0 NONE 4
ATOM 1 C 0 3.598 0.080 -0.042 0.00 0.00 C+0
ATOM 2 C 0 2.092 0.036 -0.030 0.00 0.00 C+0
ATOM 3 C 0 1.452 1.160 -0.053 0.00 0.00 C+0
ATOM 4 C 0 -0.044 1.277 -0.036 0.00 0.00 C+0
ATOM 5 C 0 -0.681 -0.063 -0.413 0.00 0.00 C+0
ATOM 6 H 0 -0.509 -0.266 -1.470 0.00 0.00 H+0
ATOM 7 C 0 -2.163 -0.013 -0.142 0.00 0.00 C+0
ATOM 8 C 0 -2.665 0.246 1.255 0.00 0.00 C+0
ATOM 9 C 0 -3.014 -0.194 -1.121 0.00 0.00 C+0
ATOM 10 C 0 -0.034 -1.164 0.436 0.00 0.00 C+0
ATOM 11 C 0 1.428 -1.310 0.001 0.00 0.00 C+0
ATOM 12 H 0 3.931 1.117 -0.069 0.00 0.00 H+0
ATOM 13 H 0 3.983 -0.402 0.858 0.00 0.00 H+0
ATOM 14 H 0 3.971 -0.445 -0.922 0.00 0.00 H+0
ATOM 15 H 0 2.030 2.072 -0.087 0.00 0.00 H+0
ATOM 16 H 0 -0.373 1.565 0.962 0.00 0.00 H+0
ATOM 17 H 0 -0.355 2.039 -0.751 0.00 0.00 H+0
ATOM 18 H 0 -2.786 1.318 1.405 0.00 0.00 H+0
ATOM 19 H 0 -3.625 -0.252 1.394 0.00 0.00 H+0
ATOM 20 H 0 -1.946 -0.143 1.977 0.00 0.00 H+0
ATOM 21 H 0 -4.076 -0.159 -0.926 0.00 0.00 H+0
ATOM 22 H 0 -2.655 -0.380 -2.122 0.00 0.00 H+0
ATOM 23 H 0 -0.081 -0.889 1.490 0.00 0.00 H+0
ATOM 24 H 0 -0.558 -2.106 0.276 0.00 0.00 H+0
ATOM 25 H 0 1.466 -1.761 -0.990 0.00 0.00 H+0
ATOM 26 H 0 1.953 -1.951 0.709 0.00 0.00 H+0
CONECT 1 2 12 13 14 NONE 31
CONECT 2 1 11 3 0 NONE 32
CONECT 3 2 4 15 0 NONE 33
CONECT 4 3 5 16 17 NONE 34
CONECT 5 4 6 7 10 NONE 35
CONECT 7 5 8 9 0 NONE 36
CONECT 8 7 18 19 20 NONE 37
CONECT 9 7 21 22 0 NONE 38
CONECT 10 5 11 23 24 NONE 39
CONECT 11 10 2 25 26 NONE 40
END NONE 41
NONE 66
</inlineContents>
</jmolApplet>
</jmol>

==Uses==

Limonene has long been used to give an orange or a lemon flavour to food products (depending on what it's used with), and also to give that lovely "lemon fresh" smell to things like fairy liquid and bleach. Recently however, it has been realised that it can be used as a solvent for cleaning products on its own, leading to an explosion in "more natural" cleaning products - Mr Muscle Orange Action is a good example.(Despite the excellent marketing point that being a "more natural" product is, the reason limonene is now being used as solvent is that it is much less hazardous to health than some things that have been used as solvents in cleaning products in the past...)

==Industrial Manufacture==

Industrially, limonene is extracted as an oil from the rinds of citrus fruits (most commonly oranges, lemons and limes) and as such is produced as a by-product of the juice industry. Two grades of limonene oil are obtained; the first, food grade oil, is extracted by pressing the fruit rinds. This oil is then purified by distillation (some of the distillates can also be recovered for sale, of use as flavourings or fragrances). After this pressing process, the peel is then steamed heated; when the steam is condensed, a layer of limonene oil is left floating on its surface. This is known as technical grade limonene, and is what is used in cleaning products.

It:limonene

2006-11-21T11:29:49Z

Rpj05:

{| border="1" cellpadding="2" cellspacing="0" align="right" style="margin-left:1em; background: #ffffff;"
! colspan="2" align=center bgcolor="#ccccff" | '''Limonene'''
|-
| colspan="2" align="center" |
|-
| IUPAC nomenclature|Chemical name
| 1-methyl-4-prop-1-en-2-yl-cyclohexene
|-
| Synonyms
| 4-isopropenyl-1-methylcyclohexene<br/>Racemic: DL-limonene; dipentene
|-
| Chemical formula
| C<sub>10</sub>H<sub>16
|-
| Molecular mass
| 136.24 g/mol
|-
| Melting point
| -95.2 °C
|-
| Boiling point
| 176 °C
|-
| Density
| 0.8411 g/cm<sup>3</sup>
|-
| Refractive index
| 1.4730
|-
| Flash point
| 50°C
|-
| SMILES
| CC1=CCC(C(=C)(C))CC1
|-
|}
=Limonene=
<div align=centre>
[[image:limonene.bmp]]
</div>
Limonene is an organic molecule, one enantiomer of which smells extremely like oranges (D-limonene, the (R)- enantiomer), being the active ingredient in citrus. The other enantiomer smells like something of a cross between pine and turpentine, and unsurprisingly the molecule is classed as a "turpene".

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Nov-06 0 NONE 4
ATOM 1 C 0 3.598 0.080 -0.042 0.00 0.00 C+0
ATOM 2 C 0 2.092 0.036 -0.030 0.00 0.00 C+0
ATOM 3 C 0 1.452 1.160 -0.053 0.00 0.00 C+0
ATOM 4 C 0 -0.044 1.277 -0.036 0.00 0.00 C+0
ATOM 5 C 0 -0.681 -0.063 -0.413 0.00 0.00 C+0
ATOM 6 H 0 -0.509 -0.266 -1.470 0.00 0.00 H+0
ATOM 7 C 0 -2.163 -0.013 -0.142 0.00 0.00 C+0
ATOM 8 C 0 -2.665 0.246 1.255 0.00 0.00 C+0
ATOM 9 C 0 -3.014 -0.194 -1.121 0.00 0.00 C+0
ATOM 10 C 0 -0.034 -1.164 0.436 0.00 0.00 C+0
ATOM 11 C 0 1.428 -1.310 0.001 0.00 0.00 C+0
ATOM 12 H 0 3.931 1.117 -0.069 0.00 0.00 H+0
ATOM 13 H 0 3.983 -0.402 0.858 0.00 0.00 H+0
ATOM 14 H 0 3.971 -0.445 -0.922 0.00 0.00 H+0
ATOM 15 H 0 2.030 2.072 -0.087 0.00 0.00 H+0
ATOM 16 H 0 -0.373 1.565 0.962 0.00 0.00 H+0
ATOM 17 H 0 -0.355 2.039 -0.751 0.00 0.00 H+0
ATOM 18 H 0 -2.786 1.318 1.405 0.00 0.00 H+0
ATOM 19 H 0 -3.625 -0.252 1.394 0.00 0.00 H+0
ATOM 20 H 0 -1.946 -0.143 1.977 0.00 0.00 H+0
ATOM 21 H 0 -4.076 -0.159 -0.926 0.00 0.00 H+0
ATOM 22 H 0 -2.655 -0.380 -2.122 0.00 0.00 H+0
ATOM 23 H 0 -0.081 -0.889 1.490 0.00 0.00 H+0
ATOM 24 H 0 -0.558 -2.106 0.276 0.00 0.00 H+0
ATOM 25 H 0 1.466 -1.761 -0.990 0.00 0.00 H+0
ATOM 26 H 0 1.953 -1.951 0.709 0.00 0.00 H+0
CONECT 1 2 12 13 14 NONE 31
CONECT 2 1 11 3 0 NONE 32
CONECT 3 2 4 15 0 NONE 33
CONECT 4 3 5 16 17 NONE 34
CONECT 5 4 6 7 10 NONE 35
CONECT 7 5 8 9 0 NONE 36
CONECT 8 7 18 19 20 NONE 37
CONECT 9 7 21 22 0 NONE 38
CONECT 10 5 11 23 24 NONE 39
CONECT 11 10 2 25 26 NONE 40
END NONE 41
NONE 66
</inlineContents>
</jmolApplet>
</jmol>

==Uses==

Limonene has long been used to give an orange or a lemon flavour to food products (depending on what it's used with), and also to give that lovely "lemon fresh" smell to things like fairy liquid and bleach. Recently however, it has been realised that it can be used as a solvent for cleaning products on its own, leading to an explosion in "more natural" cleaning products - Mr Muscle Orange Action is a good example.(Despite the excellent marketing point that being a "more natural" product is, the reason limonene is now being used as solvent is that it is much less hazardous to health than some things that have been used as solvents in cleaning products in the past...)

==Industrial Manufacture==

Industrially, limonene is extracted as an oil from the rinds of citrus fruits (most commonly oranges, lemons and limes) and as such is produced as a by-product of the juice industry. Two grades of limonene oil are obtained; the first, food grade oil, is extracted by pressing the fruit rinds. This oil is then purified by distillation (some of the distillates can also be recovered for sale, of use as flavourings or fragrances). After this pressing process, the peel is then steamed heated; when the steam is condensed, a layer of limonene oil is left floating on its surface. This is known as technical grade limonene, and is what is used in cleaning products.

2006-11-20T16:02:59Z

Rpj05: /* Supplemental Project Page */

__FORCETOC__

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| bgcolor="#CCFF00" |01
| bgcolor="#CCFF00" | [[it:Lignocaine|Lignocaine (used in dentistry as a "local")]]
|-
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| bgcolor="#CCFF00" |14
| bgcolor="#66FF99" | [[it:Methoxsalen|Methoxsalen (Treatment of psoriasis)]]
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| bgcolor="#CCFF00" |20
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| bgcolor="#CCFF00" |22
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|bgcolor="#CCFF00" |23
| bgcolor="#CCFF00" | [[it:Vioxx|Vioxx (treatment of osteoarthritis symptoms and pain)]]
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| bgcolor="#CCFF00" |24
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| bgcolor="#CCFF00" |25
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*[[it:limonene]]

== [[Special:Export|Export Pages]] ==

This takes you to an '''Export''' page. A backup of the Projects area can be made (in XML) if you want to keep your own ''snapshot'' of the project pages at any instant. After you Export the page you want (ie '''It:projects''' or '''It:Lignocaine''' for example) the XML encoding of it will appear in your browser Window. You should '''view source''' for this material, copy it to a text editor, and thence save it to disk.

== Overlaps ==

If someone else starts editing a page at the same time as you, the system will detect this and offer alternatives for you to deal with. For example, it may suggest you copy the contents of the page you have been editing and merge it into the other person's page,
so that both the sets of edits are preserved. Read the on-screen instructions carefully!

Another precaution you could take is to keep a copy of the contents of the page you are editing in eg Wordpad (or Word),
make the changes there, and then copy the entire lot to the Wiki page to preview and then save. That way, if your contribution
is overlapped by someone else, you will still have a copy, and you can then resubmit it.
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--[[User:Rzepa|Rzepa]] 12:25, 19 October 2006 (BST)--[[User:Rzepa|Rzepa]] 08:31, 5 November 2006 (UTC)

== Wiki Utillities ==
Utilities have been written to help the conversion of material from HTML.

# [http://diberri.dyndns.org/wikipedia/html2wiki/ A HTML2Wiki Converter]

No wiki2html converter suitable for use has yet been identified.
=== Wiki Templates ===

[[Template:DOI]] and [[Template:Doi-inline]] are providea as (protected) templates for your use. Many other templates exist, often to be found on e.g. Wikipedia pages. You may decide one of these is of particular use, or of interest. If so, you can install it on the wiki here for you and others to use. Add below a line that looks like {{template-name|parameter}}, save, and click on the red text to create the new template. If you prefer the task of adding useful templates to that of adding information about molecules, then you will be given full credit for performing this valuable service for others!
--[[User:Rzepa|Rzepa]] 14:41, 20 October 2006 (BST)

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[[Template:Chem-Data]]

[[Template:Chembox supplement]] - to be linked to from the supplementary section of the table in the template above, for usage see [[Template_talk:chembox_supplement|here]]

[[Template:NFPA_704]] - for notes on how to use, see [[Template_talk:NFPA_704|here]]

[[R & S Phrases]]