1.0 2010-04-08 22:11:21 UTC 2025-11-19 00:48:02 UTC FDB014586 (S)-p-Menth-1-en-4-ol α-Terpinene-4-ol, also known as terpinen-4-ol, 1-para-menthen-4-ol or p-Menth-1-en-4-ol or 4-carvomenthenol, is an isomer of terpineol. It 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. α-Terpinene-4-ol is a hydrophobic, largely neutral molecule that is essentially insoluble in water. It has a peppery, spicy, musty, citrus odor and a cooling woody or spicy taste. α-Terpinene-4-ol is widely used as a flavoring agent and as a masking agent in cosmetics. α-Terpinene-4-ol is a natural product that can be found in a number of plants, such as allspice, anise, apple, basil, cardamom, cinnamon and Melaleuca alternifolia (also called tea tree) and is the main bioactive component of tea tree oil (PMID 22083482). Terpinen-4-ol is a potent bactericidal agent that also possess antifungal properties. In particular, it has shown in vitro activity against Staphylococcus aureus and C. albicans (PMID: 27275783). It has also been shown that combining this natural substance and conventional drugs may help treat resistant yeast and bacterial infections. Several studies have suggested that terpinen-4-ol induces antitumor effects by selectively causing necrotic cell death and cell-cycle arrest in melanoma cell lines, or by triggering caspase-dependent apoptosis in human melanoma cells (PMID: 27275783). (+)-Terpinen-4-ol (S)-(+)-p-Menth-1-en-4-ol (S)-1-Isopropyl-4-methyl-3-cyclohexen-1-ol (S)-p-Menth-1-en-4-ol S-4-carvomenthenol S-Origanol C10H18O 154.253 154.1357652 (1S)-4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol (1S)-1-isopropyl-4-methylcyclohex-3-en-1-ol 2438-10-0 CC(C)[C@]1(O)CCC(C)=CC1 InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3/t10-/m1/s1 WRYLYDPHFGVWKC-SNVBAGLBSA-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 Hydrocarbon derivatives Monocyclic monoterpenoids Tertiary alcohols Alcohol Aliphatic homomonocyclic compound Hydrocarbon derivative Monocyclic monoterpenoid Organic oxygen compound Organooxygen compound P-menthane monoterpenoid Tertiary alcohol logp 2.81 ALOGPS logs -1.79 ALOGPS solubility 2.50e+00 g/l ALOGPS logp 2.33 ChemAxon pka_strongest_acidic 20 ChemAxon pka_strongest_basic -0.61 ChemAxon iupac (1S)-4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol ChemAxon average_mass 154.253 ChemAxon mono_mass 154.1357652 ChemAxon smiles CC(C)[C@]1(O)CCC(C)=CC1 ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3/t10-/m1/s1 ChemAxon inchikey WRYLYDPHFGVWKC-SNVBAGLBSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 48.31 ChemAxon polarizability 18.7 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsIr 7007 Specdb::MsIr 7008 Specdb::MsIr 7009 Specdb::CMs 5607 Specdb::CMs 44580 Specdb::CMs 159199 Specdb::MsMs 93741 Specdb::MsMs 93742 Specdb::MsMs 93743 Specdb::MsMs 157566 Specdb::MsMs 157567 Specdb::MsMs 157568 Specdb::MsMs 2746948 Specdb::MsMs 2746949 Specdb::MsMs 2746950 Specdb::MsMs 2932374 Specdb::MsMs 2932375 Specdb::MsMs 2932376 Specdb::NmrOneD 132678 Specdb::NmrOneD 132679 Specdb::NmrOneD 132680 Specdb::NmrOneD 132681 Specdb::NmrOneD 132682 Specdb::NmrOneD 132683 Specdb::NmrOneD 132684 Specdb::NmrOneD 132685 Specdb::NmrOneD 132686 Specdb::NmrOneD 132687 Specdb::NmrOneD 132688 Specdb::NmrOneD 132689 Specdb::NmrOneD 132690 Specdb::NmrOneD 132691 Specdb::NmrOneD 132692 Specdb::NmrOneD 132693 Specdb::NmrOneD 132694 Specdb::NmrOneD 132695 Specdb::NmrOneD 132696 Specdb::NmrOneD 132697 HMDB35823 #<Reference:0x000055ce31cf8488> Apple Type 1 specific Malus pumila 283210 Carrot Type 1 specific Daucus carota ssp. sativus 79200 chocolate grapefruit lemon lime minty pepper