p-Menthane-3,8-diol

p-Menthane-3,8-diol
Names
	Preferred IUPAC name 2-(2-Hydroxypropan-2-yl)-5-methylcyclohexan-1-ol
	Other names 2-(1-Hydroxy-1-methylethyl)-5-methylcyclohexanol; para-Menthane-3,8-diol; 2-Hydroxy-α,α,4-trimethylcyclohexanemethanol
Identifiers
CAS Number	42822-86-6;
3D model (JSmol)	Interactive image;
Beilstein Reference	2552262
ChEBI	CHEBI:48250;
ChEMBL	ChEMBL3120644;
ChemSpider	484204;
ECHA InfoCard	100.050.849
EC Number	255–9537;
KEGG	C02904;
PubChemCID	556998;
UNII	6T6Z1Z1NC4;
CompTox Dashboard(EPA)	DTXSID0035744;
	InChI InChI=1S/C10H20O2/c1-7-4-5-8(9(11)6-7)10(2,3)12/h7-9,11-12H,4-6H2,1-3H3 Key: LMXFTMYMHGYJEI-UHFFFAOYSA-N; InChI=1/C10H20O2/c1-7-4-5-8(9(11)6-7)10(2,3)12/h7-9,11-12H,4-6H2,1-3H3 Key: LMXFTMYMHGYJEI-UHFFFAOYAL;
	SMILES OC(C1CCC(CC1O)C)(C)C;
Properties
Chemical formula	C10H20O2
Molar mass	172.268g·mol−1
Density	1.009 g/cm3
	Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa). verify(what is?) Infobox references

p-Menthane-3,8-diol,also known aspara-menthane-3,8-diol,PMD,ormenthoglycol,is anorganic compoundclassified as adioland aterpenoid.It is colorless. Its name reflects the hydrocarbon backbone, which is that ofp-menthane.A total of eightstereoisomersare possible, based on the three stereocenters of the ring. Depending on the source, one or more may predominate.

PMD is the active ingredient in someinsect repellents.Its odor and chemical structure are similar tomenthol,and it has a cooling feel.^[1]It is found in small quantities in theessential oilfrom the leaves ofCorymbia citriodora,formerly known asEucalyptus citriodora.This tree is native toAustralia,but is now cultivated in many warm places around the world.C. citriodoraoil, when refined to increase its PMD content for use in insect repellents, is known in the United States asoil of lemon eucalyptus(OLE).^[2]C. citriodoraoil contains only 1–2% PMD, while refined OLE contains approximately up to 70% PMD.^[3]Some commercial PMD products are not made fromC. citriodoraoil, but rather from syntheticcitronellal.

Effectiveness

A 2006 study showed that PMD used as a repellent is as effective asDEETwhen used in like quantities.^[4]

Contraindications

PMD should not be used on children under 3 years of age.^[5]

Interactions

Few if any studies have evaluated possible interactions when using PMD with sunscreens.^[6]

Chemistry

There are eight possiblestereoisomers.^[7]The exact composition is rarely specified and is commonly assumed to be a complex mixture. PMD can be synthesized by aPrins reactionofcitronellal.^[3]

Refined OLE contains approximately up to 70% PMD, a mixture of thecisandtransisomersofp-menthane-3,8-diol.

History

Its repellent effect was discovered in the 1960s by the industry.^[vague]

OLE has been notified under the EuropeanBiocidal Products Directive(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 theHealth and Safety Executivein the UK. It is also registered with Canada'sPest Management Regulatory Agencyunder the generic name "PMD and related oil of lemon eucalyptus compounds".

References

^John C. Leffingwell."Cool without menthol & cooler than menthol and cooling compounds as insect repellents".Leffingwell & Associates.
^"Home".citrepel.co.uk.
^^a ^bDrapeau, Jeremy (2011)."Green synthesis ofpara-Menthane-3,8-diol fromEucaplytus citriodora:Application for repellent products ".Comptes Rendus Chimie.14(7–8): 629–635.doi:10.1016/j.crci.2011.02.008.
^Carroll, Scott P.; Loye, Jenella (2006)."PMD, a Registered Botanical Mosquito Repellent with Deet-Like Efficacy".Journal of the American Mosquito Control Association.22(3): 507–13.doi:10.2987/8756-971X(2006)22[507:PARBMR]2.0.CO;2.PMID 17067054.S2CID 225645.
^"Prevent Mosquito Bites".Centers for Disease Control and Prevention.Retrieved24 September2023.
^"Insect Repellents".National Pesticide Information Center. February 2018.Archivedfrom the original on 13 September 2023.Retrieved26 September2023.Few or no studies address using IR3535 or oil of lemon eucalyptus with sunscreens.
^PubChem Compound Search

[1] John C. Leffingwell."Cool without menthol & cooler than menthol and cooling compounds as insect repellents".Leffingwell & Associates.

[2] "Home".citrepel.co.uk.

[crc2011-3] Drapeau, Jeremy (2011)."Green synthesis ofpara-Menthane-3,8-diol fromEucaplytus citriodora:Application for repellent products ".Comptes Rendus Chimie.14(7–8): 629–635.doi:10.1016/j.crci.2011.02.008.

[4] Carroll, Scott P.; Loye, Jenella (2006)."PMD, a Registered Botanical Mosquito Repellent with Deet-Like Efficacy".Journal of the American Mosquito Control Association.22(3): 507–13.doi:10.2987/8756-971X(2006)22[507:PARBMR]2.0.CO;2.PMID 17067054.S2CID 225645.

[5] "Prevent Mosquito Bites".Centers for Disease Control and Prevention.Retrieved24 September2023.

[6] "Insect Repellents".National Pesticide Information Center. February 2018.Archivedfrom the original on 13 September 2023.Retrieved26 September2023.Few or no studies address using IR3535 or oil of lemon eucalyptus with sunscreens.

[7] PubChem Compound Search

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