1.0 2010-04-08 22:11:35 UTC 2019-11-26 03:11:05 UTC FDB014996 p-Menthane-3,8-diol Constituent of the roots of Litsea cubeba (mountain pepper) p-Menthane-3,8-diol, also known as para-menthane-3,8-diol and PMD, is an active ingredient used in insect repellents. It smells similar to menthol and acts as a coolant. PMD is found in the oil within leaves of the Eucalyptus citriodora tree. This tree is native to Australia, but is now cultivated in many warm places around the world. This oil, when refined for use in insect repellents, is known as Oil of Lemon Eucalyptus or, more commonly, Citriodiol. Typically, Citriodiol contains 64% PMD (a mixture of the cis and trans isomers of p-menthane-3,8-diol). Citriodiol has been notified under the European Biocidal Products Directive (BPD) 98/8/EC and is currently proceeding through the registration process with the Heath and Safety Executive in the UK. It is the only natural ingredient that can now be used as an insect repellent. (1Alpha,3beta,4beta)-p-menthane-3,8-diol 2-(1-Hydroxy-1-methylethyl)-5-methylcyclohexanol 2-(2-Hydroxy-2-propyl)-5-methyl-cyclohexanol 2-(2-hydroxypropan-2-yl)-5-methylcyclohexan-1-ol 2-Hydroxy-a,a,4-trimethylcyclohexanemethanol, 9CI 2-Hydroxy-alpha,alpha,4-trimethyl-cyclohexanemethanol 2-Hydroxy-alpha,alpha,4-trimethylcyclohexanemethanol cis-1,3,trans-1,4-P-Menthane-3,8-diol Cubebaol Cyclohexanemethanol, 2-hydroxy-alpha,alpha,4-trimethyl- Cyclohexanol, 2-(2-hydroxy-2-propyl)-5-methyl- Isopulegol hydrate Menthoglycol p-Menthane-3,8-diol, cis-1,3,trans-1,4- C10H20O2 172.268 172.146329884 2-(2-hydroxypropan-2-yl)-5-methylcyclohexan-1-ol p-menthane-3,8-diol 42822-86-6 CC1CCC(C(O)C1)C(C)(C)O InChI=1S/C10H20O2/c1-7-4-5-8(9(11)6-7)10(2,3)12/h7-9,11-12H,4-6H2,1-3H3 LMXFTMYMHGYJEI-UHFFFAOYSA-N belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Menthane monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homomonocyclic compounds Cyclic alcohols and derivatives Cyclohexanols Hydrocarbon derivatives Monocyclic monoterpenoids Tertiary alcohols Alcohol Aliphatic homomonocyclic compound Cyclic alcohol Cyclohexanol Hydrocarbon derivative Monocyclic monoterpenoid Organic oxygen compound Organooxygen compound P-menthane monoterpenoid Secondary alcohol Tertiary alcohol a small molecule p-menthane monoterpenoid logp 1.88 ALOGPS logs -1.21 ALOGPS solubility 1.06e+01 g/l ALOGPS logp 1.23 ChemAxon pka_strongest_acidic 14.61 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac 2-(2-hydroxypropan-2-yl)-5-methylcyclohexan-1-ol ChemAxon average_mass 172.268 ChemAxon mono_mass 172.146329884 ChemAxon smiles CC1CCC(C(O)C1)C(C)(C)O ChemAxon formula C10H20O2 ChemAxon 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 ChemAxon inchikey LMXFTMYMHGYJEI-UHFFFAOYSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 49.18 ChemAxon polarizability 20.41 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 5880 Specdb::CMs 44749 Specdb::CMs 153033 Specdb::NmrOneD 133878 Specdb::NmrOneD 133879 Specdb::NmrOneD 133880 Specdb::NmrOneD 133881 Specdb::NmrOneD 133882 Specdb::NmrOneD 133883 Specdb::NmrOneD 133884 Specdb::NmrOneD 133885 Specdb::NmrOneD 133886 Specdb::NmrOneD 133887 Specdb::NmrOneD 133888 Specdb::NmrOneD 133889 Specdb::NmrOneD 133890 Specdb::NmrOneD 133891 Specdb::NmrOneD 133892 Specdb::NmrOneD 133893 Specdb::NmrOneD 133894 Specdb::NmrOneD 133895 Specdb::NmrOneD 133896 Specdb::NmrOneD 133897 Specdb::MsMs 8201 Specdb::MsMs 8202 Specdb::MsMs 8203 Specdb::MsMs 10679 Specdb::MsMs 10680 Specdb::MsMs 10681 Specdb::MsMs 12368 Specdb::MsMs 12369 Specdb::MsMs 12370 Specdb::MsMs 14873 Specdb::MsMs 14874 Specdb::MsMs 14875 Specdb::MsMs 17351 Specdb::MsMs 17352 Specdb::MsMs 17353 Specdb::MsMs 19040 Specdb::MsMs 19041 Specdb::MsMs 19042 Specdb::MsMs 2811932 Specdb::MsMs 2811933 Specdb::MsMs 2811934 Specdb::MsMs 2896722 Specdb::MsMs 2896723 Specdb::MsMs 2896724 HMDB36145 48250 #<Reference:0x000055ce32fcaef8> Fruits Unknown generic eucalyptus herbal minty