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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
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

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(1S)-(+)-3-Carene 99%

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(S)-(+)-Carvone

assay

99%

assay

95%

assay

97%

assay

96%

form

liquid

form

solid

form

liquid

form

liquid

refractive index

n20/D 1.472 (lit.)

refractive index

-

refractive index

n20/D 1.562 (lit.)

refractive index

n20/D 1.497 (lit.)

bp

170-172 °C (lit.)

bp

-

bp

96-97 °C/8 mmHg (lit.)

bp

96-98 °C/10 mmHg (lit.)

density

0.865 g/mL at 25 °C (lit.)

density

-

density

1.038 g/mL at 25 °C (lit.)

density

0.96 g/mL at 25 °C (lit.)

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

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 Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

116.6 °F - closed cup

Flash Point(C)

47 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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