6153-17-9

Basic information

• Product Name: 3-methylidene-6-propan-2-yl-cyclohexene
• Synonyms: (R)-3-Isopropyl-6-methylene-1-cyclohexene;(R)-p-Mentha-1(7),2-diene;[R,(-)]-3-Methylene-6-(1-methylethyl)cyclohexene;beta-Phellandrene L-form
• CAS NO: 6153-17-9
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23
• Mol File: 6153-17-9.mol

Chemical Properties

• Boiling Point: bp758 178-179°; bp12 53°
• Flash Point: 44°C
• Appearance: /
• Density: d1515 0.8497
• Vapor Pressure: 1.57mmHg at 25°C
• Refractive Index: nD20 1.4800
• CAS DataBase Reference: 3-methylidene-6-propan-2-yl-cyclohexene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methylidene-6-propan-2-yl-cyclohexene(6153-17-9)
• EPA Substance Registry System: 3-methylidene-6-propan-2-yl-cyclohexene(6153-17-9)

Safety Data

• Hazardous Substances Data: 6153-17-9(Hazardous Substances Data)

Usage

Definition

ChEBI: A beta-phellandrene in which the chiral centre has R configuration.

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

Upstream product

• 763-10-0 geranyl diphosphate 
• 2158-59-0 (R)-(-)-cryptone 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 100190-37-2 (S)-4-iso-propyl-1-trimethylsilyloxy-1-cyclohexene 
• 60-29-7 diethyl ether 
• 3247-45-8 1,2,3,7-tetrabromo-p-menthane 
• 7553-56-2 iodine 
• 5989-27-5 D-limonene 

Downstream Products

• 18465-95-7 (1R)-7anti-isopropyl-5-methyl-bicyclo[2.2.2]oct-5-ene-2endo,3endo-dicarboxylic acid-anhydride 
• 23963-70-4 (S)-4-Isopropyl-cyclohex-1-enecarbaldehyde 
• 3247-45-8 1,2,3,7-tetrabromo-p-menthane 

Relevant articles and documents

Total syntheses of (+)-adunctins C and D: Assignment of their absolute configurations

The first total synthesis of (+)-adunctin C (ent-1) and (+)-adunctin D (2), two monoterpene-substitued dihydrochalcones isolated from Piper aduncum (Piperaceae), was achieved. A regioselective oxidative [3 + 2] cycloaddition of acylphloroglucinol with (-)-β-phellandrene was developed to construct their unique spirobenzofuran skeleton. The absolute configurations of natural adunctins 1 and 2 were thus assigned through these endeavors. This journal is

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.

TRANSFORMATIONS OF p-MENTHADIENES UNDER THE ACTION OF POTASSIUM tert-BUTANOLATE IN DIMETHYL SULFOXIDE

The products of the transformation of α- and γ-terpinenes, terpinolene, (+)-trans-isolimonene, and (+)-limonene under the action of potassium tert-butanolate in dimethyl sulfoxide contained - in addition to the α- and γ-terpinenes, isoterpinolene, p-mentha-3,8-diene and p-cymene found previously - terpinolene, α- and β-phellandrenes, p-mentha-2,4-diene (in total amount of 1-3percent), and polymers.Under these conditions, limonene is racemized.The primary products of the isomerization reaction have been identified.A supplementary scheme for the isomerization transformations of p-menthadienes is presented.