464-48-2

Basic information

• Product Name: (-)-CAMPHOR
• Synonyms: (-)-Alcanfor;(1s,4s)-(-)-campho;7,7-trimethyl-(1s)-bicyclo(2.2.1)heptan-2-on;7,7-trimethyl-(1s)-bicyclo[2.2.1]heptan-2-on;Camphor, (1S,4S)-(-)-;Camphor, l-, (-)-;CAMPHORE;Levo-(-)-camphor
• CAS NO: 464-48-2
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23
• EINECS: 207-354-7
• Product Categories: Miscellaneous Natural Products;Bicyclic Monoterpenes;Biochemistry;Camphor, etc. (Plasticizer);Functional Materials;Plasticizer;Terpenes
• Mol File: 464-48-2.mol
• Article Data: 105

Chemical Properties

• Melting Point: 177-179 °C(lit.)
• Boiling Point: 204 °C(lit.)
• Flash Point: 148 °F
• Appearance: White to yellow/Adhering Crystals or Crystalline Powder
• Density: 0.990
• Vapor Density: 5.24 (vs air)
• Vapor Pressure: 4 mm Hg ( 70 °C)
• Refractive Index: -44 ° (C=20, EtOH)
• Storage Temp.: Store below +30°C.
• Explosive Limit: 0.6-4.5%(V)
• Water Solubility: Soluble in water. (0.34 g/L) at 20°C
• Stability: Stable. Incompatible with strong reducing agents, strong oxidizing agents, chlorinated solvents. Protect from direct sunlight.
• Merck: 14,1732
• BRN: 4291747
• CAS DataBase Reference: (-)-CAMPHOR(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-CAMPHOR(464-48-2)
• EPA Substance Registry System: (-)-CAMPHOR(464-48-2)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26
• RIDADR: UN 2717 4.1/PG 3
• WGK Germany: 1
• RTECS: EX1250000
• TSCA: Yes
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 464-48-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 464-48-2 differently. You can refer to the following data:
1. (1S,4S)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one also known by its common name as (-)-Camphor is a chiral intermediate of camphor and is used as a flavour additive in foods and sweetners.
2. (1S)-(-)-Camphor is used as chiral intermediate and chiral auxiliary precursor. It is used in the synthesis of high-potency sweeteners. It acts as catalytic agent and petrochemical additive.

Chemical Properties

white crystals

Definition

ChEBI: The S-enantiomer of camphor.

General Description

Colorless or white crystals. Fragrant and penetrating odor. Slightly bitter and cooling taste. Odor index at 68°F: 40. Flash point 149°F. Burns with a bright, smoky flame. Sublimes appreciably at room temperature and pressure; 14% sublimes within 60 minutes at 176°F and 12 mm Hg.

Reactivity Profile

(-)-CAMPHOR may be sensitive to heat and direct sunlight. Incompatible with strong oxidizing agents, strong reducing agents and chlorinated solvents. Also incompatible with potassium permanganate. Salts of any kind should not be added to (-)-CAMPHOR in water. Reacts violently with chromic anhydride .

Fire Hazard

(-)-CAMPHOR is flammable.

InChI:InChI=1/C10H16O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7H,4-6H2,1-3H3/t7-,10+/m0/s1

Upstream product

• 76-29-9 3-bromocamphor 
• 791787-82-1 endo-borneol 
• 124-76-5 (+)-borneol 
• 464-43-7 d-borneol 
• 736109-58-3 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 124-76-5 iso-borneol 
• 124-76-5 endo-borneol 
• 76-29-9 (1S,4S)-3-bromo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 464-43-7 borneol 
• 881024-40-4 (-)-Borneol 
• 756834-48-7 C₁₆H₃₂OSi 
• 5655-61-8 bornyl acetate 
• 64474-54-0 (-)-(1S,3R,4R)-3-bromocamphor 
• 91-60-1 2-Naphthalenethiol 

Downstream Products

• 145514-75-6 (1S,2S,4S)-1,7,7-trimethyl-2-(2'-pyridinyl)bicyclo[2.2.1]heptan-2-ol 
• 153829-39-1 C₂₅H₄₀N₂O₂S 
• 68330-44-9 2-methylisoborneol 
• 508-32-7 tricyclene 
• 5794-04-7 camphene 
• 759457-76-6 N-isobornylaniline 
• 75946-22-4 N-bornylaniline 
• 464-45-9 endo-borneol 
• 464-43-7 borneol 
• 79-92-5 (+)-camphene 
• 124-83-4 D-(+)-camphoric acid 
• 10334-26-6 (R)-camphorquinone 
• 2767-84-2 (1S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione 
• 251645-83-7 3-(hydroxyimino)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 

Relevant articles and documents

Photoinduced Formation of Hybrid Aryl Pd-Radical Species Capable of 1,5-HAT: Selective Catalytic Oxidation of Silyl Ethers into Silyl Enol Ethers

A direct visible light-induced generation of a hybrid aryl Pd-radical species from aryl iodide and Pd(0) is reported to enable an unprecedented (for hybrid Pd-radical species) hydrogen atom-transfer event. This approach allowed for efficient desaturation of readily available silyl ethers into synthetically valuable silyl enols. Moreover, this oxidation reaction proceeds at room temperature without the aid of exogenous photosensitizers or oxidants.

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Ruthenium-on-Carbon-Catalyzed Facile Solvent-Free Oxidation of Alcohols: Efficient Progress under Solid-Solid (Liquid)-Gas Conditions

A protocol for the ruthenium-on-carbon (Ru/C)-catalyzed solvent-free oxidation of alcohols, which proceeds efficiently under solid-solid (liquid)-gas conditions, was developed. Various primary and secondary alcohols were transformed to corresponding aldehydes and ketones in moderate to excellent isolated yields by simply stirring in the presence of 10% Ru/C under air or oxygen conditions. The solvent-free oxidation reactions proceeded efficiently regardless of the solid or liquid state of the substrates and reagents and could be applied to gram-scale synthesis without loss of the reaction efficiency. Furthermore, the catalytic activity of Ru/C was maintained after five reuse cycles.

carba Nicotinamide Adenine Dinucleotide Phosphate: Robust Cofactor for Redox Biocatalysis

Here we report a new robust nicotinamide dinucleotide phosphate cofactor analog (carba-NADP+) and its acceptance by many enzymes in the class of oxidoreductases. Replacing one ribose oxygen with a methylene group of the natural NADP+ was found to enhance stability dramatically. Decomposition experiments at moderate and high temperatures with the cofactors showed a drastic increase in half-life time at elevated temperatures since it significantly disfavors hydrolysis of the pyridinium-N?glycoside bond. Overall, more than 27 different oxidoreductases were successfully tested, and a thorough analytical characterization and comparison is given. The cofactor carba-NADP+ opens up the field of redox-biocatalysis under harsh conditions.

Molecular cloning and functional characterization of a two highly stereoselective borneol dehydrogenases from Salvia officinalis L

Enzymes for selective terpene functionalization are of particular importance for industrial applications. Pure enantiomers of borneol and isoborneol are fragrant constituents of several essential oils and find frequent application in cosmetics and therapy. Racemic borneol can be easily obtained from racemic camphor, which in turn is readily available from industrial side-streams. Enantioselective biocatalysts for the selective conversion of borneol and isoborneol stereoisomers would be therefore highly desirable for their catalytic separation under mild reaction conditions. Although several borneol dehydrogenases from plants and bacteria have been reported, none show sufficient stereoselectivity. Despite Croteau et al. describing sage leaves to specifically oxidize one borneol enantiomer in the late 70s, no specific enzymes have been characterized. We expected that one or several alcohol dehydrogenases encoded in the recently elucidated genome of Salvia officinalis L. would, therefore, be stereoselective. This study thus reports the recombinant expression in E. coli and characterization of two enantiospecific enzymes from the Salvia officinalis L. genome, SoBDH1 and SoBDH2, and their comparison to other known ADHs. Both enzymes produce preferentially (+)-camphor from racemic borneol, but (?)-camphor from racemic isoborneol.