441619
(1S)-(+)-3-Carene
99%
Synonym(s):
(+)-3-Carene, (1S)-3,7,7-Trimethylbicyclo[4.1.0]hept-3-ene
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About This Item
Empirical Formula (Hill Notation):
C10H16
CAS Number:
Molecular Weight:
136.23
UNSPSC Code:
12352205
NACRES:
NA.22
PubChem Substance ID:
EC Number:
207-856-6
Beilstein/REAXYS Number:
1902767
MDL number:
Assay:
99%
Form:
liquid
Quality Level
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
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.
signalword
Danger
hcodes
Hazard Classifications
Aquatic Acute 1 - Aquatic Chronic 1 - Asp. Tox. 1 - Flam. Liq. 3 - Skin Irrit. 2 - Skin Sens. 1
Storage Class
3 - Flammable liquids
flash_point_f
116.6 °F - closed cup
flash_point_c
47 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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Brown, H.C. et al.
The Journal of Organic Chemistry, 53, 2911-2911 (1988)
Sonawane, H.R. et al.
Synlett, 875-875 (1993)
Dulcere, J.-P. et al.
The Journal of Organic Chemistry, 58, 5702-5702 (1993)