CAS 495-60-3 (-)-Zingiberene (HCID 92776)

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Basic information

CAS: 495-60-3
Standard SMILES: CC(C)=CCC[C@H](C)[C@@H]1C=CC(C)=CC1
InChIKey: KKOXKGNSUHTUBV-LSDHHAIUSA-N
Molecular formula: C15H24
Average molar mass: 204.35 g/mol
Monoisotopic mass: 204.18780077

Overview

Zingiberene is 2-Methylcyclohexa-1,3-diene in which a hydrogen at the 5 position is substituted (R configuration) by a 6-methyl-hept-5-en-2-yl group (S configuration). It is a sesquiterpene found in the dried rhizomes of Indonesian ginger, Zingiber officinale. It is a sesquiterpene and a cyclohexadiene. It is an enantiomer of an ent-zingiberene.

Names & identifiers

Preferred name: (-)-Zingiberene
IUPAC: (5R)-2-methyl-5-[(2S)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene
English name: [S-(R*,S*)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene
Molecular formula: C15H24
Molecular weight: 204.35

Names & synonyms

Zingiberene495-60-3(5R)-2-methyl-5-[(2S)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene(-)-Zingiberene8XOC63EI5FCHEBI:10115DTXSID00197808(5R)-2-methyl-5-((2S)-6-methylhept-5-en-2-yl)cyclohexa-1,3-dieneRefChem:196099DTXCID20120299207-804-2a-zingiberene

Show more names

α-Zingiberene1,3-Cyclohexadiene, 5-(1,5-dimethyl-4-hexenyl)-2-methyl-, (S-(R*,S*))-α-zingiberene,[S-(R,S)]-5-(1,5-dimethyl-4-hexenyl)-2-methyl-1,3-cyclohexadiene,(-)-zingiberenel-Zingiberene(-)-ZingebereneZingiberene (7CI)(R)-5-[(S)-1,5-Dimethyl-4-hexenyl]-2-methyl-1,3-cyclohexadiene(R)-2-Methyl-5-((S)-6-methylhept-5-en-2-yl)-cyclohexa-1,3-diene

(-)-alpha-zingiberene.alpha.-SesquiphellandreneZingiberene from ginger(R)-2-Methyl-5-((S)-6-methylhept-5-en-2-yl)cyclohexa-1,3-dieneUNII-8XOC63EI5F(S-(R*,S*))-5-(1,5-Dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-dieneEINECS 207-804-2| cent-Zingiberene

Properties

Computed structural properties

XLogP: 5.2
Topological polar surface area: 0 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 0
Rotatable bonds: 4
Heavy atoms: 15
Formal charge: 0
Complexity: 274

Experimental & physicochemical properties

LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C15 isoprenoids (sesquiterpenes) [PR0103]

Physicochemical properties

Boiling point: 128 · 128-129 °C(Press: 9 Torr)
Density: 0.8713 g/cm3 · 0.8713 g/cm3
storage temp.: -86 °C · Amber Vial, -86°C Freezer, Under inert atmosphere
solubility: Chloroform (Slightly), Hexane (Slightly), Methanol (Slightly)
form: Oil
color: Colourless
Odor: 10 % · at 10.00 % in dipropylene glycol. spice fresh sharp
Odor Type: spicy
Stability: Light Sensitive, Temperature Sensitive
InChI: InChI=1/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-10,14-15H,5,7,11H2,1-4H3/t14-,15+/s3
InChIKey: KKOXKGNSUHTUBV-HRCJQKRTNA-N
SMILES

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H304 (81.2%): May be fatal if swallowed and enters airways [Danger Aspiration hazard]

P261, P264, P272, P273, P280, P301+P316, P302+P352, P321, P331, P332+P317, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 16 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAsp. Tox. 1 (81.2%)

Safety data

Signal word: Danger
Symbol(GHS): GHS08,GHS07,GHS09
Hazard statements: H315-H319-H317-H411-H304
Precautionary statements: P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362

Chemistry & industry

Applications

Usesα-Zingiberene is a sesquiterpine found in leaf glandular trichomes that is currently being evaluated for its cytotoxicity towards human tumour cell lines.

Suppliers33 total

成都超九八生物科技有限公司13348960310 13348960310 · [email protected]

艾吉析科技（上海）有限公司17717235263 · [email protected]

Henan Rane Chemical Co., Ltd.+86-18738066252 · [email protected]

上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]

安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]

Related reactions

4 records

New reaction record

HRID 522434As productAs reactantuspto-grants-2016_05

HRID 590684As productuspto-grants-2016_01

HRID 1530189As productuspto-grants-2015_07

HRID 2201341As productAs reactantuspto-grants-2016_06

Compound notes

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