(4R)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane

• ChemBase ID: 119300
• Molecular Formular: C10H16O
• Molecular Mass: 152.23344
• Monoisotopic Mass: 152.12011513
• SMILES: C12(OC1C[C@H](C(=C)C)CC2)C
• Canonical SMILES: CC(=C)[C@@H]1CCC2(C(C1)O2)C
• InChI: InChI=1S/C10H16O/c1-7(2)8-4-5-10(3)9(6-8)11-10/h8-9H,1,4-6H2,2-3H3/t8-,9?,10?/m1/s1
• InChIKey: CCEFMUBVSUDRLG-XNWIYYODSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane
• IUPAC Traditional name: (+)-limonene oxide
• Synonyms: (4R)-1-Methyl-4-(1-methylethenyl)-7-oxabicyclo[4.1.0]heptane; (R)-Limonene Epoxide; (R)-Limonene 1,2-epoxide (Mixture of Diastereomers); (+)-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; (+)-Limonene 1,2-epoxide; (4R)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane; (+)-Limonene oxide, mixture of cis and trans; (+)-对薄荷-1,8-二烯 1,2-环氧化物; (4R)-1,2-环氧-对薄荷-8-烯; (4R)-4-异丙烯基-1-甲基-1-环己烯 1,2-环氧化物; (+)-柠檬烯 1,2-环氧化物; (+)-氧化柠檬烯（顺反异构体混合物）

Database IDs

• CAS Number: 203719-54-4
• MDL Number: MFCD00074770
• Beilstein Number: 80231
• PubChem SID: 24850373; 24853059; 162107485
• PubChem CID: 441245

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.3190312
• LogD (pH = 7.4): 2.3190312
• Log P: 2.3190312
• Molar Refractivity: 45.2408 cm^3
• Polarizability: 18.148024 Å^3
• Polar Surface Area: 12.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ether
• Apperance: Colourless oil
• Boiling Point: 113-114 °C/50 mmHg(lit.)
• Flash Point: 149 °F; 65 °C
• Density: 0.929 g/mL at 25 °C(lit.); 0.930 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.466(lit.); n20/D 1.467
• Optical Rotation: [α]20/D +70.5±3°, neat; [α]22/D +69°, neat

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (sum of isomers, GC); 97%
• Optical Purity: ee: 98% (GLC)
• Description: 2 Isomers
• Empirical Formula (Hill Notation): C10H16O
• Classification: Genuine Natural Compounds

DETAILS

InterBioScreen - BB_NC-0643

2 Isomers

Sigma Aldrich - 218324

Packaging
50 g in glass bottle

Sigma Aldrich - 17763

Packaging
100 mL in glass bottle

Toronto Research Chemicals - L461750

Oxidized Limonene, a common reagent used in the preparation of fragrant compounds.

REFERENCES

• D'Souza, A., et al.: J. Nat. Prod., 67, 700 (2004)
• Bergstroem, M., et al.: Chem. Res. Toxicol., 19, 760 (2004)
• Krishnamurthy, M., et al.: Bioorg. Med. Chem., 16, 6489 (2004)