ChemicalBook Product Catalog Biochemical Engineering Plant extracts (-)-P-MENTHA-1,5-DIENE

(-)-P-MENTHA-1,5-DIENE

Product Name(-)-P-MENTHA-1,5-DIENE
CAS4221-98-1
MFC10H16
MW136.23
EINECS224-167-6
MOL File4221-98-1.mol

Chemical Properties

alpha	D20 -217°
Boiling point	171-174 °C(lit.)
Density	0.844 g/mL at 20 °C(lit.)
vapor pressure	2.35hPa at 20℃
refractive index	n20/D 1.475
Flash point	49 °C
storage temp.	2-8°C
solubility	Benzene (Sparingly), Ethyl Acetate (Slightly)
form	clear liquid
color	Colorless to Light yellow to Light orange
Odor	at 100.00 %. terpene spicy medicinal
Odor Type	terpenic
optical activity	[α]20/D 225±5°, c = 10% in diethyl ether
Water Solubility	4.37mg/L at 20℃
Merck	14,7200
BRN	2497824
Henry's Law Constant	3.4×10^-4 mol/(m³Pa) at 25℃, Schuhfried et al. (2015)
Cosmetics Ingredients Functions	PERFUMING
InChI	1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3/t10-/m1/s1
InChIKey	OGLDWXZKYODSOB-SNVBAGLBSA-N
SMILES	CC(C)[C@H]1CC=C(C)C=C1
LogP	5.74 at 21.6℃
CAS DataBase Reference	4221-98-1(CAS DataBase Reference)
EPA Substance Registry System	1,3-Cyclohexadiene, 2-methyl-5-(1-methylethyl)-, (5R)- (4221-98-1)

Safety Information

Risk Statements	10
RIDADR	UN 2319 3/PG 3
WGK Germany	3
F	23
TSCA	TSCA listed
HS Code	2902.19.0050
HazardClass	3
PackingGroup	III
Storage Class	3 - Flammable liquids
Hazard Classifications	Aquatic Acute 1 Aquatic Chronic 1 Asp. Tox. 1 Flam. Liq. 3 Skin Sens. 1B

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

()-α-Phellandrene is a colorless liquid with a citrus odor and a slight peppery note. It is isolated, for example, from Eucalyptus dives oil. Pinenes are widespread, naturally occurring terpene hydrocarbons. The α- and β-forms occur in varying ratios in essential oils.

Uses

(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.

Definition

ChEBI: (-)-alpha-phellandrene is the (R)-(-)-stereoisomer of alpha-phellandrene. It is an enantiomer of a (+)-alpha-phellandrene.

General Description

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

Flammability and Explosibility

Flammable

Purification Methods

Purify it by gas chromatography on an Apiezon column. Also purify it by steam distillation (with 0.5% hydroquinone), then re-distil it through a 50 plate bubble cap column b 72-72.5o/22mm [Pines & Eschinazi J Am Chem Soc 77 6318 1955]. UV: max 263nm ( 3,345) in octane. [Read & Storey J Chem Soc 2770 1930, Beilstein 5 III 341, 5 IV 436.]

Toxics Screening Level

The screening level is being set at the default of 0.1 μg/m3 with annual averaging.

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