alpha-CYCLOHEXYLMANDELIC ACID

PRODUCT IDENTIFICATION
CAS NO. 4335-77-7

alpha-CYCLOHEXYLMANDELIC ACID

EINECS NO. 224-380-4
FORMULA C6H5C(OH)(C6H11)COOH
MOL WT. 234.29

H.S. CODE

  

TOXICITY

  
SYNONYMS alpha-cyclohexyl-hydroxyphenylacetic acid;
alpha-Cyclohexylmandelsäure; ácido alpha-Ciclohexilmandélico; Acide -alpha-Cyclohexylmandélique; alpha-Cyclohexyl-alpha-hydroxybenzeneacetic acid; (±)-Cyclohexylphenylglycolic acid; Acide phenylcyclohexylhydroxyacetique; Hexahydrobenzilic acid; Lespedamine; Phenyl-cyclohexylglycolic acid; alpha-Phenylcyclohexaneglycolic acid; alpha-Cyclohexylmandelic acid;
DERIVATION

 

CLASSIFICATION

  

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE white crystalline powder
MELTING POINT 162 - 167 C
BOILING POINT  
SPECIFIC GRAVITY  
SOLUBILITY IN WATER  
pH  
VAPOR DENSITY  

AUTOIGNITION

 

NFPA RATINGS

 Health: 1 Flammability: 1 Reactivity: 0

REFRACTIVE INDEX

 

FLASH POINT

 

STABILITY Stable under ordinary conditions

GENERAL DESCRIPTION AND APPLICATIONS
The Grignard Reaction is the organometallic halide (mainly alkyl- or aryl- magnesium halides) addition to a ketone or acid chlorides to form a tertiary alcohol. The reaction with formaldehyde and aldehyde yields a primary alcohol and secondary alcohol respectively. It is unreasonable to expect oxidation reaction of tertiary alcohols which don't have a hydrogen atom attached to alpha carbon. Tertiary alcohol can yield alkenes (dehydration reaction) and alkyl halide (SN1 reaction) in the presence of acid catalyst. Cyclohexylphenylglycolic acid is a tertiary alcohol which benzene, cyclohexane and acetic acid are attached to alpha carbon. This compound is an alpha-hydroxy acid which has a hydroxyl group on the carbon atom next to the acid group. In structure this compound belong to mandelic acid.

Mandelic Acid, phenylglycollic acid, is an alpha-hydroxy acid (AHA) which has a hydroxyl group on the carbon atom next to the acid group. If the hydroxy group is on the second carbon next to the acid group, it is called beta-hydroxy acid. Glycolic acid  is the simplest AHA which has dual functionality of alcohol and acid in a low mole weight structure. Because of its small molecular weight and size, it has a better capability to penetrate skin. AHA is used extensively in cosmetics. It is known that it diminishes the lines on the skin and make skins look young by acting as a humectant to absorb moisture in air and by exfoliating action to break the bonds between dead skin cells. Mandelic Acid ( alpha-hydroxybenzeneacetic acid) is the smallest AHA among compounds which have aromatic group. It has an asymmetric carbon atom and thus has two chiral isomers; the dextro-, levo-. The D- and L-mandelic acid are enantiomers (also called enantiomorph; each molecule is asymmetrical and has the mirror image of the other) affect pharmaceutical activity. It is a white crystalline compound; melting at 118 C; partially soluble in water; freely soluble in isopropyl and ethyl alcohol; darkening upon exposure to light. Its structure provide the bacteriostatic property. It is excreted well in the urine. It is used as a antiseptic ingredient particularly against urinary tract infections. Mandelic acid and its derivatives are used to apply the dual activities as an antibacterial agent and as an antiaging agent (AHA activity) similar to glycolic acid. It is used as an intermediate for the synthesis of target molecules for other applications.

SALES SPECIFICATION

APPEARANCE

 white crystalline powder
ASSAY

99.0% min

MELTING POINT

162 - 167 C
MOISTURE 0.5% max
TRANSPORTATION
PACKING
 
HAZARD CLASS  
UN NO.  
OTHER INFORMATION
Hazard Symbols: XI, Risk Phrases:36/37/38, Safety Phrases: 24/25/28A-37-45