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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.

signalword

Danger

Hazard Classifications

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

wgk_germany

WGK 3

flash_point_f

closed cup

flash_point_c

closed cup

ppe

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
David F Lima et al.
The Journal of pharmacy and pharmacology, 64(2), 283-292 (2012-01-10)
The aim of this work was to investigate the antinociceptive property of α-phellandrene (α-PHE) in experimental nociception models and possible mechanisms involved. Mass spectrometry was used to evaluate the purity and molecular mass of α-PHE. Macrophages from mice peritoneal cavity
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
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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