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Revision as of 11:00, 10 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi← Previous edit Latest revision as of 20:31, 8 March 2024 edit undoSarbz (talk | contribs)Extended confirmed users942 editsm Copyediting 
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{{Short description|Chemical compound found in oil of lemon eucalyptus}}
{{DISPLAYTITLE:''p''-Menthane-3,8-diol}} {{DISPLAYTITLE:''p''-Menthane-3,8-diol}}
{{Chembox {{Chembox
| Watchedfields = changed
| verifiedrevid = 444037735 | verifiedrevid = 444039089
| Name = ''p''-Menthane-3,8-diol | Name = ''p''-Menthane-3,8-diol
| ImageFile = Para-Menthane-3,8-diol chemical structure.png | ImageFile = P-menthane-3,8-diol (PMD).svg
| ImageSize = 120px | ImageSize = 120px
| ImageFile2 = P-menthane-3,8-diol 3D BS.png
| IUPACName = 2-(1-Hydroxy-1-methylethyl)-5-methylcyclohexanol
| ImageSize2 = 120px
⚫ | OtherNames = ''para''-Menthane-3,8-diol; 2-Hydroxy-α,α,4-trimethylcyclohexanemethanol
| PIN = 2-(2-Hydroxypropan-2-yl)-5-methylcyclohexan-1-ol
⚫ | Section1 = {{Chembox Identifiers
⚫ | OtherNames = 2-(1-Hydroxy-1-methylethyl)-5-methylcyclohexanol<br />''para''-Menthane-3,8-diol<br />2-Hydroxy-α,α,4-trimethylcyclohexanemethanol
⚫ |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 484204 | ChemSpiderID = 484204
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LMXFTMYMHGYJEI-UHFFFAOYSA-N | StdInChIKey = LMXFTMYMHGYJEI-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 42822-86-6 | CASNo = 42822-86-6
| EINECS = 255–9537 | EINECS = 255–9537
| PubChem = | PubChem =556998
| Beilstein = 2552262
| UNII = 6T6Z1Z1NC4
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 48250 | ChEBI = 48250
| DTXSID = DTXSID0035744
| KEGG = C02904
| ChEMBL = 3120644
| SMILES = OC(C1CCC(CC1O)C)(C)C | SMILES = OC(C1CCC(CC1O)C)(C)C
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=10|H=20|O=2 | C=10 | H=20 | O=2
| Appearance = | Appearance =
| Density = | Density = 1.009 g/cm<sup>3</sup>
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = }} | Solubility = }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = }} | AutoignitionPt = }}
}} }}


'''''p''-Menthane-3,8-diol''', also known as '''''para''-menthane-3,8-diol''', '''PMD''', or '''menthoglycol''', is an ] classified as a ] and a ]. It is colorless. Its name reflects the hydrocarbon backbone, which is that of ]. A total of eight ]s are possible, based on the three stereocenters of the ring. Depending on the source, one or more may predominate.
'''''p''-Menthane-3,8-diol''', also known as '''''para''-menthane-3,8-diol''', '''PMD''', or '''Menthoglycol''', is an active ingredient used in ]s. It smells similar to ] and acts as a ]<ref></ref>. PMD is found in very small quantities in the ] within leaves of the '']'' tree. This tree is native to ], but is now cultivated in many warm places around the world. This oil, when refined for use in insect repellents, is known in the United States as ''oil of lemon eucalyptus'' or under the registered tradename ''Citriodiol''. This refined oil contains approximately 64% PMD (a mixture of the ''cis'' and ''trans'' ]s of ''p''-menthane-3,8-diol). The refined oil has been notified under the European ] (BPD) 98/8/EC under its trade name ''Citriodiol'' (PMDRBO) and is currently proceeding through the registration process with the ] in the UK. It is the only natural derived active ingredient that can now be used as an insect repellent in the United States and Europe.


PMD is the active ingredient in some ]s. Its odor and chemical structure are similar to ], and it has a cooling feel.<ref>{{cite web | url = http://www.leffingwell.com/cooler_than_menthol.htm | title = Cool without menthol & cooler than menthol and cooling compounds as insect repellents | author = John C. Leffingwell | publisher = Leffingwell & Associates}}</ref> It is found in small quantities in the ] from the leaves of '']'', formerly known as ''Eucalyptus citriodora''. This tree is native to ], but is now cultivated in many warm places around the world. ''C. citriodora'' oil, when refined to increase its PMD content for use in insect repellents, is known in the United States as ''oil of lemon eucalyptus'' (OLE).<ref>{{cite web |url=https://www.citrepel.co.uk/ |title=Home |website=citrepel.co.uk}}</ref> ''C. citriodora'' oil contains only 1–2% PMD, while refined OLE contains approximately up to 70% PMD.<ref name="crc2011"/> Some commercial PMD products are not made from ''C. citriodora'' oil, but rather from synthetic ].
Because there are R and S configurations possible at carbon atoms 1, 2, and 5, PMD has eight possible stereoisomers. Each of these, and many of the possible mixtures, have their own CID number.<ref>PubChem Compound Search = http://www.ncbi.nlm.nih.gov/sites/entrez?db=pccompound&cmd=Link&LinkName=pccompound_pccompound_sameconnectivity_pulldown&from_uid=556998</ref>. However, the isomeric composition is rarely specified and is commonly assumed to be racemic.


==Effectiveness==
The ] has recognized Oil of Lemon Eucalyptus (OLE) as the only effective naturally derived substance for deterring ] carrying ]. PMD can be synthetically manufactured; however, one study has found that repellents containing synthetic PMD mixtures are not as effective as those containing naturally derived PMD mixtures (oil of lemon eucalyptus).<ref>{{Cite journal| journal = Journal of the American Mosquito Control Association | volume = 22 | issue = 3 | pages = 507–13 | year = 2006 | doi = 10.2987/8756-971X(2006)222.0.CO;2 | title = PMD, a Registered Botanical Mosquito Repellent with Deet-Like Efficacy | last1 = Carroll | first1 = Scott P. | last2 = Loye | first2 = Jenella | pmid=17067054}}</ref> This study also shows that naturally-derived PMD is as effective as ] when used in like quantities. A 2006 study showed that PMD used as a repellent is as effective as ] when used in like quantities.<ref>{{Cite journal| journal = Journal of the American Mosquito Control Association | volume = 22 | issue = 3 | pages = 507–13 | year = 2006 | doi = 10.2987/8756-971X(2006)222.0.CO;2 |url= https://www.researchgate.net/publication/6729297 | title = PMD, a Registered Botanical Mosquito Repellent with Deet-Like Efficacy | last1 = Carroll | first1 = Scott P. | last2 = Loye | first2 = Jenella | pmid=17067054| s2cid = 225645 }}</ref>

==Contraindications==
PMD should not be used on children under 3 years of age.<ref>{{cite web |title=Prevent Mosquito Bites |url=https://www.cdc.gov/zika/prevention/prevent-mosquito-bites.html |publisher=Centers for Disease Control and Prevention |access-date=24 September 2023}}</ref>

==Interactions==
Few if any studies have evaluated possible interactions when using PMD with sunscreens.<ref>{{cite web |title=Insect Repellents |url=http://npic.orst.edu/factsheets/repellents.html |publisher=National Pesticide Information Center |access-date=26 September 2023 |archive-url=https://web.archive.org/web/20230913011642/http://npic.orst.edu/factsheets/repellents.html |archive-date=13 September 2023 |date=February 2018 |url-status=live |quote=Few or no studies address using IR3535 or oil of lemon eucalyptus with sunscreens.}}</ref>

==Chemistry==
There are eight possible ]s.<ref></ref> The exact composition is rarely specified and is commonly assumed to be a complex mixture. PMD can be synthesized by a ] of ].<ref name="crc2011">{{Cite journal| journal = Comptes Rendus Chimie | volume = 14 | issue = 7–8 | pages = 629–635 | year = 2011 | doi = 10.1016/j.crci.2011.02.008 | title = Green synthesis of ''para''-Menthane-3,8-diol from ''Eucaplytus citriodora'': Application for repellent products | last1 = Drapeau | first1 = Jeremy | url = https://comptes-rendus.academie-sciences.fr/chimie/articles/10.1016/j.crci.2011.02.008/ }} {{open access}}</ref>

Refined OLE contains approximately up to 70% PMD, a mixture of the ''cis'' and ''trans'' ]s of ''p''-menthane-3,8-diol.

==History==
Its repellent effect was discovered in the 1960s by the industry.{{vague|date=June 2023}}

OLE has been notified under the European ] (BPD) 98/8/EC (now BPR Regulation (EU) No. 528/212) under its generic name "PMD rich botanic oil" and is currently proceeding through the registration process with the ] in the UK. It is also registered with Canada's ] under the generic name "PMD and related oil of lemon eucalyptus compounds".

==See also==
* ]
* ] (IR3535)
* ]
* ], a ] ] that can be applied to clothing to help prevent bites


==References== ==References==
<references/> <references/>


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