(+)-Dihydrocarvone

HCID 22227
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Basic information

CAS
5524-05-0
Standard SMILES
C=C(C)[C@@H]1CC[C@@H](C)C(=O)C1
InChIKey
AZOCECCLWFDTAP-UHFFFAOYSA-N
Molecular formula
C10H16O
Average molar mass
152.23 g/mol

Overview

(+)-dihydrocarvone is a dihydrocarvone in (R,R) configuration. It is an enantiomer of a (-)-dihydrocarvone.

Names & identifiers

Preferred name
(+)-Dihydrocarvone
IUPAC
trans-(2R,5R)-2-methyl-5-prop-1-en-2-ylcyclohexan-1-one
English name
(+)-DIHYDROCARVONE MIXTURE OF ISOMERS
Molecular formula
C10H16O
Molecular weight
152.23

Names & synonyms

5524-05-0(+)-Dihydrocarvone(1R,4R)-Dihydrocarvoned-Dihydrocarvone(+)-trans-dihydrocarvonetrans-(+)-dihydrocarvone(E)-dihydrocarvone(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexanonerel-(2R,5R)-2-Methyl-5-(prop-1-en-2-yl)cyclohexan-1-one(1R,4R)-(+)-Dihydrocarvone(2R,5R)-2-methyl-5-prop-1-en-2-ylcyclohexan-1-one
Show more names
trans-DihydrocarvoneCarvone,dihydro-8-p-Menthen-2-one2R,5R-DIHYDROCARVONEp-Menth-8(9)-en-2-onep-Menth-8-en-2-one,trans-(2theta-trans)-cyclohexanon(+)-dihydrocarvone,mixtureofisomers
MFCD28125830CHEBI:154VTA43H364Z5948-04-9(+)-Dihydrocarvone (Mixture of (2S)/(2R) isomers)(2R-trans)-2-Methyl-5-(1-methylvinyl)cyclohexan-1-oneCyclohexanone, 2-methyl-5-(1-methylethenyl)-, (2R,5R)-(2R,5R)-5-Isopropenyl-2-methylcyclohexanone

Database identifiers

CAS
5524-05-0、5948-04-9
PubChem CID
22227
DTXSID
DTXSID60895818
ChEMBL
CHEMBL2268553
ChEBI
CHEBI:154
UNII
VTA43H364Z
EC Number
226-872-4、611-836-6
Nikkaji
J995.644A

Properties

Computed structural properties

XLogP
2.7
Topological polar surface area
17.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
11

Experimental & physicochemical properties

LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, (2R,5R)-) -> IFRA transparency List

Physicochemical properties

Boiling point
87 · 87-88°C/6mmHg
alpha
17 ° · +17°(22℃,neat)
Density
0.928 g/mL · 0.928 g/mL at 20 °C(lit.)
refractive index
20 · n20/D 1.471
FEMA
3565 · 3565 | P-MENTH-8-EN-2-ONE
Flash point
102 °C · 102 °C

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.

Warning

H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationChemical: Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, trans-
Hazard Classes and CategoriesAcute Tox. 4 (50%)

Safety data

PPE
Eyeshields, Gloves
wgk
3
tsca
TSCA listed
hs_code
29142900
Signal word
Warning
Symbol(GHS)
GHS07

Chemistry & industry

Uses & manufacturing

Use ClassificationFragrance Ingredients
General Manufacturing InformationCyclohexanone, 2-methyl-5-(1-methylethenyl)-, (2R,5R)-: INACTIVE
Applications · 2 items

Uses(+)-Dihydrocarvone may be used in the following processes:Synthesis of dispiro 1,2,4,5-tetraoxanes, which show potent anti-malarial activity.Synthesis of an epoxylactone by oxidation, which can undergo copolymerization with ε-caprolactone to form cross-linked copolymers with shape memory properties.Synthesis of α-Cyperone, a eudesmane type sesquiterpenoid compound with potent insecticidal activity.

General Description(+)-Dihydrocarvone, a monoterpenoid compound found in caraway oil, is a key building block to synthesize sesquiterpenes. It is generally produced either by the hydrogenation of carvone or oxidation of limonene.

Upstream & downstream products

Upstream raw materials

Suppliers100 total

陕西格列弗生物科技研究有限责任公司13892423764 · [email protected]
上海摩睿化学科技有限公司13382110328 15255501563 · [email protected]
Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
Hebei Zhuanglai Chemical Trading Co Ltd+86-16264648883 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]

Additional notes

DefinitionChEBI: A dihydrocarvone in (R,R) configuration.

Related reactions

5 records
New reaction record

Compound notes

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