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

(-)-P-MENTHA-1,5-DIENE Basic information
Product Name:(-)-P-MENTHA-1,5-DIENE
Synonyms:(R)-5-isopropyl-2-methylcyclohexa-1,3-diene;1,3-Cyclohexadiene, 2-methyl-5-(1-methylethyl)-, (5R)-;L-ALPHA-PHELLANDRENE;(5R)-2-methyl-5-propan-2-ylcyclohexa-1,3-diene;R-(-)-A-PHELLANDRENE WITH GC;(-)-α-phellandrene;(R)-2-methyl-5-(1-methylethyl)-1,3-cyclohexadiene;(-)-p-Mentha-1,5-diene, (R)-5-Isopropyl-2-methyl-1,3-cyclohexadiene
CAS:4221-98-1
MF:C10H16
MW:136.23
EINECS:224-167-6
Product Categories:Biochemistry;Monocyclic Monoterpenes;Terpenes
Mol File:4221-98-1.mol
(-)-P-MENTHA-1,5-DIENE Structure
(-)-P-MENTHA-1,5-DIENE 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
Fp 49 °C
storage temp. 2-8°C
solubility Benzene (Sparingly), Ethyl Acetate (Slightly)
form clear liquid
color Colorless to Light yellow to Light orange
Odorat 100.00 %. terpene spicy medicinal
Odor Typeterpenic
optical activity[α]20/D 225±5°, c = 10% in diethyl ether
Water Solubility 4.37mg/L at 20℃
Merck 14,7200
BRN 2497824
LogP5.74 at 21.6℃
CAS DataBase Reference4221-98-1(CAS DataBase Reference)
EPA Substance Registry System1,3-Cyclohexadiene, 2-methyl-5-(1-methylethyl)-, (5R)- (4221-98-1)
Safety Information
Risk Statements 10
RIDADR UN 2319 3/PG 3
WGK Germany 3
23
HS Code 2902.19.0050
HazardClass 3
PackingGroup III
MSDS Information
ProviderLanguage
SigmaAldrich English
(-)-P-MENTHA-1,5-DIENE 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.
DefinitionChEBI: (-)-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 ExplosibilityFlammable
Purification MethodsPurify 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.]
(-)-P-MENTHA-1,5-DIENE Preparation Products And Raw materials
R-(-)-α-Phellandrene (S)-(+)-alpha-Phellandrene METHYL CYCLOHEXADIENE P-MENTHA-6,8-DIENE-2-ONE PHELLANDRENE, -R-(-)-alpha-(SG) DL-Limonene (+)-p-mentha-1,8-diene 1,2-epoxide,(+)-p-Mentha-1,8-diene 1,2-epoxide, (4R)-1,2-Epoxy-p-menth-8-ene, (4R)-4-Isopropenyl-1-methyl-1-cyclohexene 1,2-epoxide m-Mentha-1,3-diene-5,6-dione (6CI) CIS TRANS-(4R)-P-MENTHA-2,8-DIENE-1-OL L-P-MENTHA-1,8-DIENE,(s)-(-)-p-mentha-1,8-dien (-)-P-MENTHA-1,5-DIENE Α-PHELLANDRENE ALPHA-PHELLANDRENE β-sesquiphellandrene 1,3-CYCLOHEXADIENE GAMMA-TERPINENE = P-MENTHA-1,4-DIENE 3,9-Epoxy-p-mentha-3,8-diene,p-Mentha-3,8-diene, 3,9-epoxy- (-)-P-MENTHA-1,8-DIENE-7-OL

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