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77429

Sigma-Aldrich

(R)-(−)-α-Phellandrene

≥95.0% (sum of enantiomers, GC)

Synonym(s):

(R)-(-)-alpha-Phellandrene, (−)-p-Mentha-1,5-diene, (R)-5-Isopropyl-2-methyl-1,3-cyclohexadiene

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About This Item

Empirical Formula (Hill Notation):
C10H16
CAS Number:
4221-98-1
Molecular Weight:
136.23
Beilstein/REAXYS Number:
2497824
EC Number:
224-167-6
MDL number:
MFCD00062988
UNSPSC Code:
12352002
PubChem Substance ID:
57652697
NACRES:
NA.22

Quality Level

200

assay

≥95.0% (sum of enantiomers, GC)

form

liquid

optical activity

[α]20/D −225±5°, c = 10% in diethyl ether

bp

171-174 °C (lit.)

density

0.844 g/mL at 20 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)[C@H]1CC=C(C)C=C1

InChI

1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3/t10-/m1/s1

InChI key

OGLDWXZKYODSOB-SNVBAGLBSA-N

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General description

(R)-(-)-α-Phellandrene is a monoterpene derivative.

Application

(R)-(-)-α-Phellandrene undergoes [4+2] cycloaddition with 2-naphthyl acetylenecarboxylate to form a chiral diene, which can act as a ligand for the rhodium-catalyzed asymmetric addition reactions. It may be used to synthesize (1S,5R)-5-(1-methylethyl)-2-methylidene-3-cyclohexen-1-yl hydroperoxide, which on reduction forms trans-yabunikkeol.

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Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

113.0 °F - closed cup

flash_point_c

45 °C - closed cup

ppe

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

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Chiral diene ligands for asymmetric catalysis.
Hayashi T.
Aldrichimica Acta, 42(2), 31-38 (2009)
Intrazeolite photo-oxygenation of (R)-(-)-a-phellandrene.
Stratakis M and Sofikiti N.
J. Chem. Res. (M), 2002(8), 374-375 (2002)
S Foss et al.
Systematic and applied microbiology, 21(2), 237-244 (1998-08-15)
Four pseudomonad strains 51Men, 54Pin, 62Car and 65Phen were recently isolated on the monoterpenes (+)-menthene, alpha-pinene, 2-carene and alpha-phellandrene as sole carbon source and nitrate as electron acceptor. These bacteria were characterised. The motile, mesophilic, Gram-negative rods had a strictly
Kazuhiro Okamoto et al.
Organic letters, 10(19), 4387-4389 (2008-09-06)
Chiral dienes possessing the bicyclo[2.2.2]octadiene framework were prepared readily through the [4 + 2] cycloaddition of ( R)-alpha-phellandrene with methyl propiolate as the key step. Diene 9, substituted with a tertiary alcohol on one of the two double bonds, is
Christo S Sevov et al.
The Journal of organic chemistry, 73(20), 7909-7915 (2008-09-13)
Electron transfer catalysis is an effective method for the acceleration of Diels-Alder reactions between two substrates of similar electron density. The dependence of the selectivity of the Diels-Alder reaction between (R)-alpha-phellandrene and 4-methoxystyrene catalyzed by photoinduced electron transfer with tris(4-methoxyphenyl)
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