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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:
2497824
EC Number:
224-167-6
MDL number:
MFCD00062988
UNSPSC Code:
12352002
PubChem Substance ID:
57652697
NACRES:
NA.22

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.

Signal Word

Danger

Hazard Statements

H226,H304,H317,H410

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

113.0 °F - closed cup

Flash Point(C)

45 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Intrazeolite photo-oxygenation of (R)-(-)-a-phellandrene.
Stratakis M and Sofikiti N.
J. Chem. Res. (M), 2002(8), 374-375 (2002)
Chiral diene ligands for asymmetric catalysis.
Hayashi T.
Aldrichimica Acta, 42(2), 31-38 (2009)
Gökalp İşcan et al.
Chemistry & biodiversity, 9(8), 1525-1532 (2012-08-18)
Terpene derivatives converted by microbial biotransformation constitute an important resource for natural pharmaceutical, fragrance, and aroma substances. In the present study, the monoterpene α-phellandrene was biotransformed by 16 different strains of microorganisms (bacteria, fungi, and yeasts). The transformation metabolites were
M Miyazawa et al.
Journal of agricultural and food chemistry, 48(7), 2893-2895 (2000-07-18)
gamma-Terpinene was mixed in artificial diet at a concentration of 1 mg/g of diet, and the diet was fed to the last instar larvae of common cutworm (Spodoptera litura). Metabolites were recovered from frass and analyzed spectroscopically. gamma-Terpinene was transformed
Huai-sheng Hu et al.
Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 32(1), 67-70 (2009-05-19)
The chemical constituents and antimicrobial activity of the essential oil from Acanthopanax brachypus were studied. The essential oil was extracted from the stem of A. brachypus by steam distillation, and its antimicrobial activity was tested in vitro. The chemical constituents
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