441619

Sigma-Aldrich

(1S)-(+)-3-Carene

99%

Synonym(s):
(+)-3-Carene, (1S)-3,7,7-Trimethylbicyclo4.1.0hept-3-ene
Empirical Formula (Hill Notation):
C10H16
CAS Number:
Molecular Weight:
136.23
Beilstein/REAXYS Number:
1902767
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

99%

optical activity

α20/D +17°, neat

refractive index

n20/D 1.472 (lit.)

bp

170-172 °C (lit.)

density

0.865 g/mL at 25 °C (lit.)

SMILES string

HC@@12CC=C(C)CC@1(H)C2(C)C

InChI

1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9+/m1/s1

InChI key

BQOFWKZOCNGFEC-BDAKNGLRSA-N

Related Categories

General description

(1S)-(+)-3-Carene is a monoterpene.

Application

(1S)-(+)-3-Carene has been used as a standard during the quantification of components in Lavandula stoechas essential oils by fast gas chromatography-mass spectrometry (FGC-EI/MS). It may be used as a starting material in the total synthesis of (+)-ingenol. It may also be used to synthesize (1S,3S,4S,6R)-3,7,7-trimethyl-4-morpholino-4-yl-bicyclo(4.1.0)heptano-3-ol, which can catalyze the addition of diethylzinc to different aldehydes with high enantioselectivity.
Chiral building block for the preparation of bicyclo3.2.0heptenes that are useful intermediates in the synthesis of (+)-lineatin and both enantiomers of capnellene. Has been converted to its corresponding allenyl allylic ether for studies of its thermal isomerization chemistry. Precursor to di(4-isocaranyl)borane, an asymmetric hydroboration reagent for olefins.

Packaging

1, 5 g in glass bottle

Signal Word

Warning

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xi,N

Risk Statement

10-43-50/53

Safety Statement

36/37-60-61

RIDADR

UN 2319 3 / PGIII

WGK Germany

WGK 3

Enantioselective addition of diethylzinc to aldehydes catalyzed by a ?-amino alcohol derived from (+)-3-carene.
Joshi SN and Malhotra SV.
Tetrahedron Asymmetry, 14(13), 1763-1766 (2003)
Traumatic resin defense in Norway spruce (Picea abies): methyl jasmonate-induced terpene synthase gene expression, and cDNA cloning and functional characterization of (+)-3-carene synthase.
Faldt J, et al.
Plant Molecular Biology, 51(1), 119-133 (2003)
Sonawane, H.R. et al.
Synlett, 875-875 (1993)
Brown, H.C. et al.
The Journal of Organic Chemistry, 53, 2911-2911 (1988)
Dulcere, J.-P. et al.
The Journal of Organic Chemistry, 58, 5702-5702 (1993)

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