EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

(±)-mandelic acid
benzeneacetic acid, a-hydroxy-

Sponsors

Name:2-hydroxy-2-phenylacetic acid
CAS Number: 90-64-2Picture of molecule3D/inchi
Other:15769-78-5
ECHA EINECS - REACH Pre-Reg:202-007-6
FDA UNII:NH496X0UJX
Nikkaji Web:J3.918G
Beilstein Number:510011
MDL:MFCD00064250
XlogP3:0.60 (est)
Molecular Weight:152.14936000
Formula:C8 H8 O3
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Category:antimicrobial agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 119.00 °C. @ 760.00 mm Hg
Boiling Point: 321.83 °C. @ 760.00 mm Hg (est)
Flash Point: 325.00 °F. TCC ( 162.60 °C. ) (est)
logP (o/w): 0.620
Soluble in:
 water, 1.81E+05 mg/L @ 25 °C (exp)
 water, 1.763e+005 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: antimicrobial agents
 
Suppliers:
American International Chemical, LLC.
Mandelic Acid
Jiangyin Healthway
Mandelic Acid
New functional food ingredients
Jiangyin Healthway
Mandelic Acid
M.C.Biotec
Mandelic Acid
Odor: characteristic
Use: useful in suppressing pigmentation, treating inflammatory noncystic acne, and rejuvenating photoaged skin. Moreover it has proven useful in preparing the skin for laser peeling and in helping the skin heal after laser surgery.
Penta International
MANDELIC ACID USP
Santa Cruz Biotechnology
For experimental / research use only.
DL-Mandelic acid
Sigma-Aldrich: Aldrich
For experimental / research use only.
Mandelic acid 99%
Spec-Chem Industry
SpecWhite ® DL-MA
TCI AMERICA
For experimental / research use only.
DL-Mandelic Acid >99.0%(GC)(T)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rabbit LDLo 2000 mg/kg
GASTROINTESTINAL: GASTRITIS LIVER: OTHER CHANGES GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 64, Pg. 79, 1940.

intramuscular-rat LD50 > 300 mg/kg
Experimental Medicine and Surgery. Vol. 4, Pg. 223, 1946.

intraperitoneal-rat LD50 4100 mg/kg
Bollettino Chimico Farmaceutico. Vol. 112, Pg. 53, 1973.

oral-rat LDLo 3000 mg/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 64, Pg. 79, 1940.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: antimicrobial agents
Recommendation for (±)-mandelic acid usage levels up to:
 not for fragrance use.
 
Recommendation for (±)-mandelic acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):90-64-2
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :1292
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-hydroxy-2-phenylacetic acid
Chemidplus:0000090642
RTECS:OO6300000 for cas# 90-64-2
 
References:
 2-hydroxy-2-phenylacetic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:90-64-2
Pubchem (cid):1292
Pubchem (sid):134971115
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
KEGG (GenomeNet):C01984
HMDB (The Human Metabolome Database):HMDB00703
FooDB:FDB022191
Export Tariff Code:2918.19.1200
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
 almond acid
 amygdalic acid
 amygdalinic acid
 benzeneacetic acid, a-hydroxy-
 glycolic acid, phenyl-
2-HPAA
(2RS)-2-hydroxy-2-phenylacetic acid
2-hydroxy-2-phenylacetic acid
DL-2-hydroxy-2-phenylacetic acid
(±)-2-hydroxy-2-phenylethanoic acid
2-hydroxy-2-phenylethanoic acid
a-hydroxy-a-toluic acid
 hydroxy-phenyl-acetic acid
 hydroxy(phenyl)acetic acid
DL-hydroxy(phenyl)acetic acid
(±)-a-hydroxybenzeneacetic acid
a-hydroxybenzeneacetic acid
(±)-a-hydroxyphenylacetic acid
a-hydroxyphenylacetic acid
 mandelic acid
(RS)-mandelic acid
DL-mandelic acid
racemic mandelic acid
DL-mandelicacid
 paramandelic acid
2-phenyl-2-hydroxyacetic acid
 phenylglycolic acid
2-phenylglycolic acid
DL-phenylglycolic acid
 phenylhydroxyacetic acid
a-toluic acid, a-hydroxy-
 uromaline
 

Articles:

PubMed:Alditols and monosaccharides from sorghum vinegar can attenuate platelet aggregation by inhibiting cyclooxygenase-1 and thromboxane-A2 synthase.
PubMed:Improvement of Alcaligenes faecalis nitrilase by gene site saturation mutagenesis and its application in stereospecific biosynthesis of (R)-(-)-mandelic acid.
PubMed:Derivation of safe health-based exposure limits for potential consumer exposure to styrene migrating into food from food containers.
PubMed:Oxidative decarboxylation of mandelic acid derivative by recombinant Escherichia coli: a novel method of ethyl vanillin synthesis.
PubMed:Gene cloning, expression, and characterization of a nitrilase from Alcaligenes faecalis ZJUTB10.
PubMed:Developmental toxicity of combined ethylbenzene and methylethylketone administered by inhalation to rats.
PubMed:Determination of mandelic acid enantiomers in urine by derivatization in supercritical carbon dioxide prior to their determination by gas chromatography.
PubMed:[Synthesis of new mandelic acid derivatives with preservative action. Synthesis and acute toxicity study].
PubMed:Hydrolysis of nitriles using an immobilized nitrilase: applications to the synthesis of methionine hydroxy analogue derivatives.
PubMed:Construction of an electro-enzymatic bioreactor for the production of (R)-mandelate from benzoylformate.
PubMed:Effect of chronic protein restriction on motor co-ordination and brain neurotransmitters in albino rats.
PubMed:Clinical efficacy of a chlorous acid preoperative skin antiseptic.
PubMed:Conversion of phenylalanine to benzaldehyde initiated by an aminotransferase in lactobacillus plantarum
PubMed:Broiler skin color as affected by organic acids: influence of concentration and method of application.
PubMed:An improved method for the simultaneous determination of mandelic and phenylglyoxylic acids by gas chromatography.
PubMed:Effect of food on the bioavailability of cyclandelate from commercial capsules.
PubMed:Bioavailability of cyclandelate from capsules in beagle dogs and dissolution rate: correlations with bioavailability in humans.
 
Notes:
It is an isomer of cresotinic acid (2-hydroxy-3-methylbenzoic acid) and oxymethylbenzoic acid (2-methoxybenzoic acid). Derivatives of mandelic acid are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase and catechol-o-methyl transferase. It is also present in certain skin care products, is an intermediate molecule in the production of other biochemicals, may be used as an analytical reagent and is a precursor in the manufacture of dyes. Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C8H8O3. It is a white crystalline solid that is soluble in water and most common organic solvents. [HMDB]
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