CAS 611-71-2 (-)-Mandelic acid (HCID 11914)

Names & identifiers

Preferred name: (-)-Mandelic acid
IUPAC: (2R)-2-hydroxy-2-phenylacetic acid
English name: Mandelic acid
Molecular formula: C8H8O3
Molecular weight: 152.15

Names & synonyms

611-71-2(r)-mandelic acid(R)-2-Hydroxy-2-phenylacetic acidD-Mandelic acid(-)-Mandelic acidD(-)-Mandelic acidMandelic acid, (R)-D-2-Phenylglycolic acid(-)-(R)-Mandelic acid(R)-alpha-Hydroxyphenylacetic acid(R)-alpha-Hydroxybenzeneacetic acidMandelic acid, D-

Show more names

2-Hydroxy-2-phenylacetic acid(R)-(-)-2-MANDELIC ACID(R)-(-)-mandelic(-)-D-MANDELIC ACID

(-)-alpha-Hydroxyphenylacetic acidPPL7YW1M9WCHEBI:17656RefChem:905564210-276-6(R)-(-)-Mandelic acidD-(-)-MANDELIC ACID(2R)-2-hydroxy-2-phenylacetic acid

Database identifiers

CAS: 611-71-2
PubChem CID: 11914
DTXSID: DTXSID4046523
ChEMBL: CHEMBL292411
ChEBI: CHEBI:17656
UNII: PPL7YW1M9W
EC Number: 210-276-6
Nikkaji: J43.326H

Properties

Computed structural properties

XLogP: 0.6
Topological polar surface area: 57.5 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 11
Formal charge: 0
Complexity: 138

Physicochemical properties

Melting point: 131 · 131-133 °C(lit.)
alpha: -150 · -150 º (c=2.5, H2O)
Boiling point: 214.6 °C · 214.6°C (rough estimate)
Density: 1.1677 · 1.1677 (rough estimate)
bulk density: 670 kg/m3 · 670kg/m3
refractive index: -153.5 ° · -153.5 ° (C=1, H2O)
Flash point: 190 ℃ · >190℃
storage temp.: 30 °C · Store below +30°C.
solubility: 109.8 g/l · 109.8g/l soluble
form: Crystalline Powder, Crystals or Flakes
pka: 3.37 · 3.37(at 25℃)
color: White to slightly yellow-beige
PH: 3.34 · 3.34(1 mM solution);2.75(10 mM solution);2.22(100 mM solution);
optical activity: 25 · [α]25/D 151°, c = 1 in ethanol
Water Solubility: It is partly soluble in water, freely soluble in isopropyl and ethyl alcohol.
Sensitive: Light Sensitive
BRN: 2691094 · 2691094
Stability: Stable, but light sensitive. Combustible. Incompatible with strong bases, strong oxidizing agents.
InChI: 1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m1/s1
InChIKey: IWYDHOAUDWTVEP-SSDOTTSWSA-N
SMILES: O[C@@H](C(O)=O)c1ccccc1
LogP: 0.55 · 0.550 (est)
CAS DataBase Reference: 611 · 611-71-2(CAS DataBase Reference)
FDA UNII: 7 YW1M9W · PPL7YW1M9W
ATC code: 5 CA06,J01XX06 · B05CA06,J01XX06
EPA Substance Registry System: Benzeneacetic acid, .alpha.-hydroxy-, (.alpha.R)- (611-71-2)
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 5 · GHS05
Signal word: Danger
Hazard statements: 318 · H318
Precautionary statements: 280 · P280-P305+P351+P338
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xi
Risk Statements: 41 · 41-36/37/38
Safety Statements: 22 · 22-24/25-36-26-39-37/39
WGK Germany: 1 · 1
Hazard Note: Irritant/Light Sensitive
TSCA: TSCA listed
HS Code: 29181980 · 29181980
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 1 · Eye Dam. 1
Toxicity: 50 orally · LD50 orally in Rabbit: 5000 mg/kg
REACH Registrations: Active

Safety & regulation

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 1
tsca: TSCA listed
hs_code: 29181980
Toxicity: LD50 orally in Rabbit: 5000 mg/kg
risk_code: 41-36/37/38
Signal word: Danger
Symbol(GHS): GHS05
hazard_code: Xi
hazard_note: Irritant/Light Sensitive
safety_code: 22-24/25-36-26-39-37/39
Storage Class: 11 - Combustible Solids
Hazard statements: H318
REACH Registrations: Active
Hazard Classifications: Eye Dam. 1
Precautionary statements: P280-P305+P351+P338

Chemistry & industry

Applications · 4 items

Uses(R)-(-)-Mandelic acid, 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. It is used as an intermediate for the synthesis of target molecules for other applications.

UsesAntiseptic (urinary).

Uses(R)-()-Mandelic acid can be used:As a chiral acid in the separation of diastereomeric salts for the synthesis of chiral pyridoindole based building block.In the study of chiral acid selectivity of poly(3,4-ethylenedioxythiophene) (PEDOT) based chiral conductingpolymers.

General Description(R)-(-)-Mandelic acid, a chiral resolving agent, is also used as a building block to synthesize pharmaceutical drugs such as penicillin and cephalosporin. It can be synthesized from (R,S)-mandelonitrile with high yield and enantioselectivity using nitrilase enzyme.

Upstream & downstream products

Upstream raw materials

(S)-(+)-O-Acetyl-L-mandelic acid Vinyl acetate

Downstream products

1H-Azepine-4-carboxylicacid,hexahydro-,methylester,(4R)-(9CI)(R)-3-Amino-1-(3-(Trifluoromethyl)-5,6-Dihydro-[1,2,4] Triazolo[4,3-A]Pyrazin-7(8H)-Yl)-4-(2,4,5-Trifluorophenyl) Butan-1-One Mandelate(Sgn06M)(R)-5-phenyl-1,3-dioxolane-2,4-dione (R)-2-Hydroxy-2-phenylacetohydrazide (R)-2-tert-butyl-3-Methyl-4-oxoiMidazolidin-1-iuM (R)-2-hydroxy-2-phenylacetate (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

北京华美互利生物化工010-56205725 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

INTATRADE GmbH+49 3493/605464 · [email protected]

Additional notes

DefinitionChEBI: (R)-mandelic acid is the (R)-enantiomer of mandelic acid. It has a role as a human xenobiotic metabolite. It is a conjugate acid of a (R)-mandelate. It is an enantiomer of a (S)-mandelic acid.