4221-98-1

Basic information

• Product Name: (-)-P-MENTHA-1,5-DIENE
• Synonyms: (-)-α-phellandrene;(R)-2-methyl-5-(1-methylethyl)-1,3-cyclohexadiene;1,3-cyclohexadiene,2-methyl-5-(1-methylethyl)-,(R)-;1-phellandrene;2-methyl-5-(1-methylethyl)-3-cyclohexadien(theta)-;3-Cyclohexadiene,2-methyl-5-(1-methylethyl)-,(R)-1;p-mentha-1,5-diene,(R)-(-)-;α-phellandrene,(-)-
• CAS NO: 4221-98-1
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23
• EINECS: 224-167-6
• Product Categories: Biochemistry;Monocyclic Monoterpenes;Terpenes
• Mol File: 4221-98-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 171-174 °C(lit.)
• Flash Point: 49 °C
• Appearance: Colourless to slightly yellow, mobile liquid; peppery, woody, herbaceous aroma
• Density: 0.844 g/mL at 20 °C(lit.)
• Vapor Pressure: 1.86mmHg at 25°C
• Refractive Index: n20/D 1.475
• Storage Temp.: 2-8°C
• Water Solubility: 4.37mg/L at 20℃
• Merck: 14,7200
• BRN: 2497824
• CAS DataBase Reference: (-)-P-MENTHA-1,5-DIENE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-P-MENTHA-1,5-DIENE(4221-98-1)
• EPA Substance Registry System: (-)-P-MENTHA-1,5-DIENE(4221-98-1)

Safety Data

• Statements: 10
• RIDADR: UN 2319 3/PG 3
• WGK Germany: 3
• F: 23
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 4221-98-1(Hazardous Substances Data)

Usage

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.

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.]

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

Upstream product

• 555-31-7 aluminum isopropoxide 
• 4573-50-6 (-)-piperitone 
• 67-63-0 isopropyl alcohol 
• 763-10-0 geranyl diphosphate 
• 65733-28-0 (+)-trans-piperitol 
• 2009-00-9 sabinene 
• 5989-27-5 D-limonene 
• 106-24-1 Geraniol 
• 917-64-6 methyl magnesium iodide 
• 1195-31-9 (+)-p-menth-1-ene 

Downstream Products

• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 
• 4031-53-2 (3R,4R,6S)-3,6-dihydroxymenth-1-ene 
• 4031-52-1 (1S,2S,5R)-2-methyl-5-(propan-2-yl)cyclohex-3-ene-1,2-diol 
• 99-82-1 Menthane 
• 99-87-6 4-methylisopropylbenzene 
• 111822-11-8 linderatone 
• 123357-16-4 (R)-5,7-Dihydroxy-8-((1R,6R)-6-isopropyl-3-methyl-cyclohex-2-enyl)-2-phenyl-chroman-4-one 
• 123297-92-7 neolinderatone 
• 123406-75-7 (R)-5,7-Dihydroxy-6,8-bis-((1R,6R)-6-isopropyl-3-methyl-cyclohex-2-enyl)-2-phenyl-chroman-4-one 
• 120523-25-3 (3S,4R)-8,9-dihydro-o-cannabidiol 
• 120523-27-5 (1S,3S,4R)-8,9-dihydro-o-iso-tetrahydrocannabinol 
• 120523-26-4 (1S,3S,4R)-8,9-dihydro-p-iso-tetrahydrocannabinol 
• 23050-49-9 (3S,4R)-8,9-dihydro-p-cannabidiol 
• 122-03-2 (4-isopropylbenzaldehyde) 

Relevant articles and documents

High-Throughput Synthesis of (S)-α-Phellandrene through Three-Step Sequential Continuous-Flow Reactions

The combination of continuous-flow processing with heterogeneous catalysts allows for efficient, sustainable, multistep synthesis. Here, we report the continuous-flow synthesis of a valuable terpene product, phellandrene, from a readily available natural feedstock. The protocol consists of selective hydrogenation using a highly active and stable supported platinum catalyst, dehydrative hydrazone formation, followed by the Shapiro reaction. Appropriate design of the reactor allowed for high productivity and space-time yield. Phellandrene was synthesized on a 30-g scale over 6 h, giving high yields, purity, and productivity.

Triphenylpyrylium tetrafluoroborate-sensitized photochemistry of the terpenes sabinene, α-phellandrene, and α- and γ-terpinene

The triphenypyrylium tetrafluoroborate (TPT)-sensitized reactions of several terpene donor molecules, including sabinene (1), α-phellandrene (4), α-terpinene (5) and γ-terpinene (6) give rise to significantly different products than reactions induced by other electron-transfer sensitizers, such as 1,4-dicyanobenzene (DCB). The divergent reactions require decidedly different key intermediates; the products obtained with TPT can be explained by dissociative recombination of the intermediate radical-radical cation pair in the triplet state, generating donor-derived biradicals.

Isotopically Sensitive Branching as a Tool for Evaluating Multiple Product Formation by Monoterpene Cyclases

The deuterated substrates geranyl pyrophosphate and geranyl pyrophosphate were employed to examine isotopically sensitive branching in the biosynthesis of monoterpene olefin isomers.By this method, (-)-α-pinene and (-)-β-pinene were shown to be synthesized via a common intermediate by a single cyclization enzyme from grand fir (Abies grandis), as were (-)-α-phellandrene and (-)-β-phellandrene by a single cyclase from lodgepole pine (Pinus contorta).Kinetic isotope effects were determined for the various deprotonations leading to the pinenes and phellandrenes.Key Words: Isotopically sensitive branching, monoterpene biosynthesis, monoterpene cyclase, resin biosynthesis, kinetic isotope effect.