DL-Mandelic acid

DL-Mandelic acid Basic information
Product Name:DL-Mandelic acid
Synonyms:(n)-mandelic acid;DL-MANDELIC ACID611-72-3;MANDELICACIDANDITSCOMMONSALTS;alpha-Hydroxyphenylacetic acid;Kyselina 2-fenyl-2-hydroxyethanova;Kyselina mandlova;kyselina2-fenyl-2-hydroxyethanova;kyselinamandlova
CAS:90-64-2
MF:C8H8O3
MW:152.15
EINECS:202-007-6
Product Categories:Pharmaceutical intermediates;Building Blocks;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;C8;Carbonyl Compounds;Carboxylic Acids;Pyridines ,Halogenated Heterocycles;90-64-2
Mol File:90-64-2.mol
DL-Mandelic acid Structure
DL-Mandelic acid Chemical Properties
Melting point 119-121 °C (lit.)
Boiling point 214.6°C (rough estimate)
alpha [α]D20 -0.5~+0.5° (c=2, H2O)
density 1.30
vapor pressure 0.01 Pa (50 °C)
refractive index 1.4810 (estimate)
storage temp. Store below +30°C.
solubility 139g/l
pka3.85(at 25℃)
form Crystals or Crystalline Powder
color White
PH2.3 (10g/l, H2O)
Odorfaint odor
optical activity[α]/D 0±1°, c = 5 in H2O
Water Solubility 150 g/L (20 ºC)
Sensitive Light Sensitive
Merck 14,5717
BRN 510011
InChIKeyIWYDHOAUDWTVEP-UHFFFAOYSA-N
LogP0.5 at 23℃
CAS DataBase Reference90-64-2(CAS DataBase Reference)
NIST Chemistry ReferenceBenzeneacetic acid, «alpha»-hydroxy-(90-64-2)
EPA Substance Registry SystemMandelic acid (90-64-2)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 36/37/38-22
Safety Statements 22-24/25-37/39-26-36
WGK Germany 3
RTECS OO6300000
TSCA Yes
HS Code 29181990
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
DL-Mandelic acid Usage And Synthesis
Chemical PropertiesWhite rhomboidal crystals, decompose when exposed to light. Soluble in ether and isopropanol, soluble in ethanol and water; R-form melting point is 133°C, [α]-159.73° (ethanol), gradually racemic at 160°C. S-form melting point is 133.8°C, [α]+156.57° (water).
UsesOrganic synthesis, medicine (urinary antiseptic).
UsesDL-Mandelic acid may be used as an analytical reference standard for the determination of DL-mandelic acid in:
Human urine samples by high performance liquid chromatography (HPLC) equipped with ultraviolet (UV) detector.
Rat urine samples by gas chromatography-mass spectrometry (GC-MS) with selected ion monitoring (SIM) detection.
PreparationMandelic acid can be prepared by the hydrolysis of amygdalin with sulfuric acid or of mandelonitrile with hydrochloric acid. The mandelonitrile can be prepared by the action of hydrocyanic acid on benzaldehyde, and by the action of sodium or potassium cyanide on the sodium bisulfite addition product of benzaldehyde. The procedure described differs from earlier methods in that the sodium bisulfite addition compound of benzaldehyde is prepared in the presence of sodium cyanide and the nitrile is formed immediately.
synthesis of mandelic acid
DefinitionChEBI: Mandelic acid is a 2-hydroxy monocarboxylic acid that is acetic acid in which two of the methyl hydrogens are substituted by phenyl and hydroxyl groups. It has a role as an antibacterial agent and a human xenobiotic metabolite. It is a 2-hydroxy monocarboxylic acid and a member of benzenes. It derives from an acetic acid. It is a conjugate acid of a mandelate. Exists in stereoisomeric forms. The properties are those of the dl-form.
General DescriptionDL-Mandelic acid is an aromatic hydrocarbon metabolite of styrene.
HazardToxic by ingestion.
Flammability and ExplosibilityNotclassified
Safety ProfilePoison by intramuscular route. Moderately toxic by ingestion. Continued absorption can cause kidney irritation. When heated to decomposition it emits acrid smoke and irritating fumes.
DL-Mandelic acid Preparation Products And Raw materials
Raw materialsAcetone-->Sodium cyanide-->Sodium bisulfite-->Benzaldehyde-->Glycolonitrile-->2-Chloroacetophenone-->Benzoylformic acid
Preparation Products1,2-Phenylenediacetic acid-->DL-alpha-Methoxyphenylacetic acid-->Pemoline
4-Hydroxy-DL-mandelic acid 4-CHLORO-DL-MANDELIC ACID,P-CHLORO-DL-MANDELIC ACID,4-CHLORO-DL-MANDELIC ACID 98+% Benzilic acid Ethyl 2-(Chlorosulfonyl)acetate Phenethyl phenylacetate Ascoric Acid DL-MANDELIC ACID METHYL ESTE 4-Hydroxyphenylglycolic acid 3,4-(Methylenedioxy)-DL-mandelic acid 2-Methylphenylacetic acid DL-3,4-DihydroxyMandelic acid DL-MANDELIC ACID BENZYL ESTER DL-MANDELIC ACID BENZYL ESTER 98+% DL-MANDELIC ACID ETHYL ESTER 93+%,DL-MANDELIC ACID ETHYL ESTER phosphoric acid CHLOROPHOSPHONAZO III 4-Hydroxy-3-methoxymandelic acid Mandelic acid

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