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441619

Sigma-Aldrich

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

99%

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Synonym(s):
(+)-3-Carene, (1S)-3,7,7-Trimethylbicyclo[4.1.0]hept-3-ene
Empirical Formula (Hill Notation):
C10H16
CAS Number:
498-15-7
Molecular Weight:
136.23
Beilstein:
1902767
EC Number:
207-856-6
MDL number:
MFCD00066417
UNSPSC Code:
12352205
PubChem Substance ID:
24867688
NACRES:
NA.22

Quality Level

200

Assay

99%

form

liquid

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

(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 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.

Signal Word

Danger

Hazard Statements

H226,H304,H315,H317,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Asp. Tox. 1 - Flam. Liq. 3 - Skin Irrit. 2 - Skin Sens. 1

WGK

WGK 3

Flash Point(F)

116.6 °F

Flash Point(C)

47 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

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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
Dulcere, J.-P. et al.
The Journal of Organic Chemistry, 58, 5702-5702 (1993)
Sonawane, H.R. et al.
Synlett, 875-875 (1993)
Brown, H.C. et al.
The Journal of Organic Chemistry, 53, 2911-2911 (1988)
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)
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