441619

Sigma-Aldrich

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

99%

Synonym(s):
(+)-3-Carene, (1S)-3,7,7-Trimethylbicyclo[4.1.0]hept-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

Quality Level

assay

99%

optical activity

[α]20/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

[H][C@@]12CC=C(C)C[C@]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

Chiral building block for the preparation of bicyclo[3.2.0]heptenes 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.
(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.

Packaging

1, 5 g in glass bottle

Signal Word

Warning

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2319 3 / PGIII

WGK Germany

WGK 3

Dulcere, J.-P. et al.
The Journal of Organic Chemistry, 58, 5702-5702 (1993)
Xiaofeng Zhu et al.
Environmental entomology, 49(3), 586-592 (2020-03-22)
Scolytus schevyrewi Semenov (Coleoptera: Curculionidae: Scolytinae) is native to China and Central Asia. Damage by the adults and larvae weakens local apricot trees (Armeniaca spp.), often causing death to many host trees. In previous studies, freshly cut apricot logs were...
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)
Lavandula stoechas essential oil from Spain: Aromatic profile determined by gas chromatography-mass spectrometry, antioxidant and lipoxygenase inhibitory bioactivities.
Carrasco A, et al.
Industrial Crops and Products, 73, 16-27 (2015)
Sonawane, H.R. et al.
Synlett, 875-875 (1993)

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