Compound: NOOTKATONE
SMILES: O=C1C=C2[C@](C[C@H](C(=C)C)CC2)(C)[C@@H](C1)C
InChIKey: WTOYNNBCKUYIKC-JMSVASOKSA-N
Synonyms: NOOTKATONE, (+)-Nootkatone, 4674-50-4, (4R,4aS,6R)-4,4a-dimethyl-6-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one, IZ2Y119N4J, DTXSID8047050, 1(10),11-Eremophiladien-2-one, 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-, DTXCID6027050, FEMA NO. 4941, CHEBI:81377, 4Betah,5alpha-eremophila-1(10),11-dien-2-one, 4betaH,5alpha-Eremorphila-1(10)11-dien-2-one, 4,4a,5,6,7,8-Hexahydro-6-isopropenyl-4,4a-dimethyl-2(3H)-naphthalenone, 4a,5-Dimethyl-1,2,3,4,4a,5,6,7-octahydro-7-keto-3-isopropenylnaphthalene, 4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone, (4R-(4alpha,4aalpha,6beta))-, 4,4A,5,6,7,8-HEXAHYDRO-6-ISO-PROPENYL-4,4A-DIMETHYL-2(3H)-NAPHTHALENONE, RefChem:854683, 225-124-4, 942-649-0, Nootkanone, (+/-)-Nootkatone, (4R,4aS,6R)-4,4a-dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one, Nootkatone, (+/-)-, Nootkatone (+/-)-form [MI], UNII-3K3OKV2A5A, 3K3OKV2A5A, MFCD04974578, 4.beta.H,5.alpha.-Eremophila-1(10),11-dien-2-one, 7betaH-Eremophila-1(10),11-dien-2-one -, (4RS,4Asr,6RS)-4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone, 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-rel, 5,6-Dimethyl-8-isopropenylbicyclo(4.4.0)dec-1-en-3-one, 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, [4R-(4.alpha.,4a.alpha.,6.beta.)]-, 28834-25-5, Nootkatone (natural), Nootkatone, (+)-, nootkaton, UNII-IZ2Y119N4J, FEMA No. 3166, (4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone; Nootkanone, 2(3H)-NAPHTHALENONE, 4,4A,5,6,7,8-HEXAHYDRO-4,4A-DIMETHYL-6-(1-METHYLETHENYL)-, (4R-(4.ALPHA.,4A.ALPHA.,6.BETA.))-, EINECS 225-124-4, Nootkatone Impurity 1, NOOTKATONE [MI], NOOTKATONE [FHFI], (+)-Nootkatone, crystalline, Nootkatone, >=98%, FG, (+)-5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one, SCHEMBL110855, CHEMBL446299, orb1303434, HSDB 8272, GLXC-19364, HY-N2195, Tox21_302385, (+)-Nootkatone, analytical standard, MFCD00036591, MSK014165, s9071, STL562310, AKOS015955823, CCG-266714, EBC-615574, (+)-Nootkatone, >=99.0% (GC), (4R,4aS,6R)-4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one, NCGC00256230-01, 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R-(4alpha,4aalpha,6beta))-, AC-34548, AS-56160, SY045912, XN168139, CAS-4674-50-4, (+)-Nootkatone, technical, >=85% (GC), CS-0019503, C17914, F862860, Q417896, 4.beta.H,5.alpha.-Eremorphila-1(10)11-dien-2-one, 7.BETA.H-EREMOPHILA-1(10),11-DIEN-2-ONE -, 5,6-DIMETHYL-8-ISOPROPENYL-BICYCLO(4,4,0)-DEC-1-EN-3-ONE, (4R,4aS,6R)-6-isopropenyl-4,4a-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one, 4,4A,5,6,7,8-HEXAHYDRO-4,4A-DIMETHYL-6-(1-METHYLENE-ETHYL)-2(3H)-NAPHTHALENONE, (4R,4aS,6R)-4,4a-Dimethyl-6-(1-propen-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one, (4R-(4alpha,4aalpha,6beta))-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylvinyl)naphthalen-2(3H)-one, 2(3H)-naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-,[4R-(4alpha,4aalpha,6beta)]-, 4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone, [4R-(4.alpha.,4a.alpha.,6.beta.)]-, 6-Isopropenyl-4,4a-dimethyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone-, [4R-(4.alpha.,4a.alpha.,6.beta.)]-
Theoretical properties:
molecular_formula: C15H22O
molecular_weight: 218.33 g/mol
exact_mass: 218.167065321 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 1
heavy_atom_count: 16
topological_polar_surface_area: 17.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from light petroleum; commercial product is a colorless to yellowish liquid
color: Crystals from light petroleum; commercial product is a colorless to yellowish liquid
odor: Grapefruit odor
boiling_point: BP: 125 °C at 0.5 mm Hg
melting_point: 36-37 °C
density: 0.9963 at 25 °C
solubility: Practically insoluble in water
flash_point: 100 °C (212 °F) - closed cup
Descriptions:
pubchem: (+)-nootkatone is a sesquiterpenoid that is 4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one which is substituted by methyl groups at positions 4 and 4a, and by an isopropenyl group at position 6 (the 4R,4aS,6R stereoisomer). It has a role as a fragrance, an insect repellent and a plant metabolite. It is a sesquiterpenoid, a carbobicyclic compound and an enone.
chebi: A sesquiterpenoid that is 4,4a,5,6,7,8-hexahydronaphthalen-2(3<em>H</em>)-one which is substituted by methyl groups at positions 4 and 4a, and by an isopropenyl group at position 6 (the 4<i>R</i>,4a<i>S</i>,6<i>R</i> stereoisomer).
chembl: NOOTKATONE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Nootkatone is an organic compound, a sesquiterpenoid, which means that it is a C15 derivative that also contains an oxygen-containing functional group (a ketone). It is the most valuable aroma compound of grapefruit. Nootkatone was originally isolated from the wood of the Alaskan yellow cedar, Cupressus nootkatensis. The species name, nootkatensis, is derived from the language of the Nuu-Chah-Nulth people of Canada (formerly referred to as the Nootka people).