(4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene

• ChemBase ID: 104246
• Molecular Formular: C10H16
• Molecular Mass: 136.23404
• Monoisotopic Mass: 136.12520051
• SMILES: CC(=C)[C@@H]1CCC(=CC1)C
• Canonical SMILES: CC1=CC[C@@H](CC1)C(=C)C
• InChI: InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m0/s1
• InChIKey: XMGQYMWWDOXHJM-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
• IUPAC Traditional name: α-limonene
• Synonyms: CARVENE; (+)-p-Mentha-1,8-diene; (+)-Carvene; (R)-4-Isopropenyl-1-methyl-1-cyclohexene; (R)-(+)-Limonene; 4-Isopropenyl-1-methyl-1-cyclohexene; p-Mentha-1,8-diene; D-LIMONENE; (4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene; (+)-对薄荷-1,8-二烯; (+)-香芹烯; (R)-4-异丙烯基-1-甲基-1-环己烯; (R)-(+)-柠檬烯

Database IDs

• CAS Number: 5989-27-5
• EC Number: 227-813-5
• MDL Number: MFCD00062991
• Beilstein Number: 2204754
• PubChem SID: 24882190; 162091432; 24851036
• PubChem CID: 440917

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.2198126
• LogD (pH = 7.4): 3.2198126
• Log P: 3.2198126
• Molar Refractivity: 46.4803 cm^3
• Polarizability: 18.013159 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -74 °C (-102 °F)
• Boiling Point: 176 °C (349 °F); 176-177 °C(lit.)
• Flash Point: 118.4 °F; 48 °C; 48 °C
• Auto Ignition Point: 237 °C (458 °F) (d,l-limonene)
• Density: 0.84 (water = 1); 0.842 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.473; n20/D 1.473(lit.)
• Vapor Pressure: <3 mmHg ( 14.4 °C); Less than 3 mm Hg (0.40 kPa) at 14 °C, 20 mm Hg at 68.2 °C
• Vapor Density: 4.7 (vs air); 4.70 (air = 1)
• Optical Rotation: [α]20/D +112±3°, c = 10% in ethanol; [α]20/D +112±5°, c = 10% in ethanol; [α]20/D +115.5±1°, c = 10% in ethanol
• Hydrophobicity(logP): 4.352

Safety Information

• Storage Condition: Room Temperature (15-30°C), Store Under Nitrogen
• RTECS: GW6360000
• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• UN Number: 2052; 2319
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 3; III
• Australian Hazchem: 3Y
• Risk Statements: 10-38-43-50/53; R:10-38-43-50/53
• Safety Statements: 24-37-60-61; S:24-37-60-61
• EU Classification: F1
• EU Hazard Identification Number: 3B
• Emergency Response Guidebook(ERG) Number: 128
• GHS Pictograms: GHS02; GHS07; GHS09
• GHS Signal Word: Warning
• Explode Limits: 6.1 %
• GHS Hazard statements: H226-H315-H317-H410
• GHS Precautionary statements: P273-P280-P501
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2052 3/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CYP1A2(1544)

Product Information

• Purity: ~90% (sum of enantiomers, GC); ≥96.0% (sum of enantiomers, GC); ≥98.0% (sum of enantiomers, GC); ≥99.0% (sum of enantiomers, GC); 95%; 97%
• Grade: analytical standard, for terpene analysis; purum; technical
• Optical Purity: ee: 98% (GLC)
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C10H16

DETAILS

MP Biomedicals - 05209995

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02155234

(4-Isopropenyl-1-methyl-1-cyclohexene; p-Mentha-1,8-diene) 1 ml = approx. 0.84 g

Sigma Aldrich - 183164

Packaging
5, 100, 500 mL in glass bottle
Application
Chiral intermediate for natural product synthesis.1
Biochem/physiol Actions
Limonene is a cyclie terpene from Chinese medicinal herb essential oils used in the synthesis of carvone. Limonene may be used as a shrinking agent to dissolve polystyrene. Limonene may be used in various insecticidal and insect repellant applications.

Sigma Aldrich - 89188

Application
biodegradable replacement solvent

Sigma Aldrich - 62118

Other Notes
Regioselective hydrogenation of the exocyclic double bond1,2; Regioselective epoxidation of the endocyclic double bond3