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441619

Sigma-Aldrich

(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:
498-15-7
Molecular Weight:
136.23
Beilstein/REAXYS Number:
1902767
EC Number:
207-856-6
MDL number:
MFCD00066417
UNSPSC Code:
12352205
PubChem Substance ID:
24867688
NACRES:
NA.22

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

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

wgk_germany

WGK 3

flash_point_f

116.6 °F - closed cup

flash_point_c

47 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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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
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)
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)
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