CAS 17199-29-0 (S)-mandelic acid (HCID 439616)

Overview

(S)-mandelic acid is a (2S)-2-hydroxy monocarboxylic acid and a mandelic acid. It is a conjugate acid of a (S)-mandelate. It is an enantiomer of a (R)-mandelic acid.

Names & identifiers

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

Names & synonyms

17199-29-0(S)-Mandelic acid(S)-2-Hydroxy-2-phenylacetic acidMandelic acid, (S)-Mandelic acid, L-D-2-Hydroxy-2-phenylacetic acid(S)-alpha-hydroxybenzeneacetic acidL0UMW58G3TCHEBI:32800DTXSID301014792RefChem:906467DTXCID601471549

Show more names

L-mandelateMANDELIC ACI(S)-Hydroxyphenylaceticacid(S)-(+)-ALPHA-HYDROXYPHENYLACETIC ACID(2S)-2-Hydroxy-2-phenylacetic Acid (L-Mandelic Acid)(S)-(+)-MandeL

241-240-8(S)-(+)-Mandelic acidL-mandelic acid(2S)-2-hydroxy-2-phenylacetic acidS-(+)-Mandelic acidL-(+)-MANDELIC ACIDMFCD00004495Atomoxetine EP Impurity E

Database identifiers

CAS: 17199-29-0、90-64-2
PubChem CID: 439616
DTXSID: DTXSID301014792
ChEMBL: CHEMBL58910
ChEBI: CHEBI:32800
UNII: L0UMW58G3T
EC Number: 241-240-8
Nikkaji: J74.069A

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

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Organic Acids

LogP0.62

Solubility181.0 mg/mL

Melting Point120 - 122 °C

Physical Description · 2 items

Off-white or white powder; [Alfa Aesar MSDS]

Solid

Dissociation Constants3.41 (at 25 °C)

Physicochemical properties

Melting point: 131 · 131-134 °C(lit.)
alpha: 155 · 155 º (c=2 , H2O)
Boiling point: 234.6 °C · 234.6°C (rough estimate)
Density: 1.341 · 1.3410
refractive index: 153.5 ° · 153.5 ° (C=1, H2O)
Flash point: 190 °C · >190°C
storage temp.: 30 °C · Store below +30°C.
solubility: Methanol (Slightly), Water (Sparingly, Heated)
form: Crystalline Powder
pka: 3.41 · 3.41±0.25(Predicted)
color: White to beige-brown
PH: 2.1 · 2.1 (60g/l, H2O, 20℃)
optical activity: 20 · [α]20/D +153±5°, c = 5% in H2O
Water Solubility: 100 g/L · 100 g/L (25 ºC)
Sensitive: Light Sensitive
BRN: 2208678 · 2208678
Stability: Stable, but light sensitive. Combustible. Incompatible with strong bases, strong oxidizing agents, strong reducing agents.
InChI: 1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1
InChIKey: IWYDHOAUDWTVEP-ZETCQYMHSA-N
SMILES: O[C@H](C(O)=O)c1ccccc1
LogP: 0.55 · 0.550 (est)
CAS DataBase Reference: 17199 · 17199-29-0(CAS DataBase Reference)
FDA UNII: 0 UMW58G3T · L0UMW58G3T
NIST Chemistry Reference: Benzeneacetic acid, «alpha»-hydroxy-, (s)-(17199-29-0)
EPA Substance Registry System: Benzeneacetic acid, .alpha.-hydroxy-, (.alpha.S)- (17199-29-0)
UNSPSC Code: 12352200 · 12352200
NACRES: 22 · NA.22
Symbol(GHS): 5 · GHS05
Signal word: Danger
Hazard statements: 318 · H318
Precautionary statements: 280 · P280-P305+P351+P338+P310
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 22 · 22-24/25-37/39-26-36
WGK Germany: 3 · 3
TSCA: TSCA listed
HS Code: 29181980 · 29181980
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 1 · Eye Dam. 1
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 1.5% (3 of 206) of reports.

Danger

H302 (26.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 206 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: Benzeneacetic acid, .alpha.-hydroxy-, (S)-

Status: Active Update: 07-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/27645

(S)-(+)-Mandelic acid: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryAn irritant that may cause serious eye injury; May cause liver and kidney injury; [Alfa Aesar MSDS] See Mandelic acid.

Hazard Classes and CategoriesAcute Tox. 4 (26.7%)

Toxicology

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

Safety data

wgk: 3
tsca: TSCA listed
hs_code: 29181980
risk_code: 36/37/38
Signal word: Danger
Symbol(GHS): GHS05
hazard_code: Xi
safety_code: 22-24/25-37/39-26-36
Storage Class: 11 - Combustible Solids
Hazard statements: H318
REACH Registrations: Active
Hazard Classifications: Eye Dam. 1
Precautionary statements: P280-P305+P351+P338+P310

Chemistry & industry

Uses & manufacturing

UsesUsed as a urinary antiseptic; [Alfa Aesar MSDS]

General Manufacturing InformationBenzeneacetic acid, .alpha.-hydroxy-, (.alpha.S)-: ACTIVE

Applications · 3 items

UsesAntiseptic (urinary).

Uses(S)-(+)-Mandelic acid is a versatile reagent used in the resolution of racemates and the preparation of amides, Pharmaceutical Intermediates.

UsesA versatile reagent used in the resolution of racemates and the preparation of amides.

Upstream & downstream products

Downstream products

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: (S)-mandelic acid is a (2S)-2-hydroxy monocarboxylic acid and a mandelic acid. It is a conjugate acid of a (S)-mandelate. It is an enantiomer of a (R)-mandelic acid.