(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

• ChemBase ID: 1518
• Molecular Formular: C10H16O
• Molecular Mass: 152.23344
• Monoisotopic Mass: 152.12011513
• SMILES: CC1(C)[C@H]2CC[C@]1(C)C(=O)C2
• Canonical SMILES: O=C1C[C@H]2C([C@]1(C)CC2)(C)C
• InChI: InChI=1S/C10H16O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7H,4-6H2,1-3H3/t7-,10+/m0/s1
• InChIKey: DSSYKIVIOFKYAU-OIBJUYFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
• IUPAC Traditional name: l-camphor
• Synonyms: (-)-Camphor; (1S)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one; (1S)-(-)-Camphor; Camphor; (-)-Camphor; (1S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one; (-)-樟脑; (1S)-1,7,7-三甲基二环[2.2.1]庚烷-2-酮; (1S)-(-)-樟脑; (-)-樟脑

Database IDs

• CAS Number: 76-22-2; 464-48-2
• EC Number: 207-354-7
• MDL Number: MFCD00064148
• Beilstein Number: 1907612
• PubChem SID: 160964975; 24892622; 46508429; 24852755; 24856901
• PubChem CID: 444294

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.5529857
• LogD (pH = 7.4): 2.5529857
• Log P: 2.5529857
• Molar Refractivity: 44.492 cm^3
• Polarizability: 17.763361 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.85
• LOG S: -2.24
• Solubility (Water): 8.80e-01 g/l

PROPERTIES

Physical Property

• Solubility: 1.6 mg/mL at 25 oC [YALKOWSKY,SH & HE,Y (2003)]
• Melting Point: 177 - 179°C; 177-179 °C(lit.)
• Boiling Point: 204 °C(lit.)
• Flash Point: 149 °F; 65 °C
• Auto Ignition Point: 870 °F
• Vapor Pressure: 4 mmHg ( 70 °C)
• Vapor Density: 5.24 (vs air)
• Optical Rotation: [α]20/D -43±1°, c = 10% in ethanol; [α]20/D -43±2°, c = 10% in ethanol; [α]20/D -43°, c = 10 in ethanol
• Hydrophobicity(logP): 2.177; 2.38 [DAYLIGHT (1999)]

Safety Information

• RTECS: EX1250000
• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 2717
• German water hazard class: 1
• Hazard Class: 4.1
• Packing Group: 3
• Risk Statements: 11-36/37/38
• Safety Statements: 16-26
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• Explode Limits: 3.5 %
• GHS Hazard statements: H228-H315-H319-H335
• GHS Precautionary statements: P210-P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2717 4.1/PG 3

Product Information

• Purity: ≥95.0% (sum of enantiomers, GC); ≥99.0% (GC); 95%; 99%
• Grade: analytical standard; purum
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C10H16O

DETAILS

DrugBank - DB01744

• Drug Groups: experimental
• Description: A bicyclic monoterpene ketone found widely in plants, especially cinnamomum camphora. It is used topically as a skin antipruritic and as an anti-infective agent. [PubChem]
• External Links: Wikipedia; Drugs.com

Sigma Aldrich - 279676

Packaging
5 g in glass bottle
Application
Chiral intermediate1 and chiral auxiliary precursor.2 Used in the synthesis of high-potency sweeteners.3

Sigma Aldrich - C352

Packaging
10 g in glass bottle

Sigma Aldrich - 21295

Other Notes
(-)-Camphor can be employed analogously to the natural (+)-camphor. Specific syntheses starting with (-)-camphor include the preparation of (-)-laurolenic acid1; analogues of cis-sativenediol and helminthosporal2; intermediates for the enantiospecific total synthesis of steroids3; and of vitamin B-124