Mandelic Acid (HCID 1292)

Names & identifiers

Preferred name: Mandelic Acid
IUPAC: 2-hydroxy-2-phenylacetic acid
English name: DL-Mandelic acid
Molecular formula: C8H8O3
Molecular weight: 152.15

Names & synonyms

MANDELIC ACIDdl-Mandelic acid2-hydroxy-2-phenylacetic acid90-64-2Phenylglycolic acidParamandelic acidAmygdalic acidUromalineRacemic mandelic acidPhenylhydroxyacetic acid(RS)-Mandelic acidalpha-Hydroxyphenylacetic acid

Show more names

DL-MandelicaciDL-MANDELSAEURE SDL-AMYGDALIC ACIDMANDELIC ACID, DL-RARECHEM AL BO 1098TIMTEC-BB SBB007730(R)(S)-MANDELICACIDMANDELIC(D,L-) ACID

Acido mandelicoKyselina mandlovaBenzeneacetic acid, alpha-hydroxy-alpha-Hydroxybenzeneacetic acidNSC-7925NH496X0UJXDTXSID6023234CHEBI:35825

Database identifiers

CAS: 611-72-3、90-64-2
PubChem CID: 1292
DTXSID: DTXSID6023234
ChEMBL: CHEMBL1609
ChEBI: CHEBI:35825
UNII: NH496X0UJX
EC Number: 202-007-6、210-277-1
Nikkaji: J2.433.033H、J2.433.034F、J3.918G

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

Density · 2 items

1.3 @25 °C

Boiling Point320 °C @760 [mm Hg]

Melting Point119 °C

Vapor Pressure0.0000164 [mmHg]

Physical Description · 2 items

Liquid

Solid; Darkens and decomposes after prolonged light exposure; [Merck Index] White crystalline powder with a faint sweet odor; [Fisher Scientific MSDS]

Kovats Retention Index1487

Physicochemical properties

Melting point: 119 · 119-121 °C(lit.)
Boiling point: 234.6 °C · 234.6°C (rough estimate)
Density: 1.289 · 1.2890
refractive index: 1.4945 · 1.4945 (estimate)
pka: 3.85 · 3.85(at 25℃)
Water Solubility: 172.5 g/L · 172.5g/L(24 ºC)
InChI: InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)
InChIKey: IWYDHOAUDWTVEP-UHFFFAOYSA-N
SMILES: C1(C=CC=CC=1)C(O)C(=O)O
CAS DataBase Reference: 611 · 611-72-3(CAS DataBase Reference)
NIST Chemistry Reference: Benzeneacetic acid, «alpha»-hydroxy-, (.+/-.)-(611-72-3)
Symbol(GHS): 7 · GHS07,GHS05
Signal word: Danger
Hazard statements: 302 · H302-H315-H318-H335
Precautionary statements: 264 · P264-P270-P301+P312-P330-P501-P280-P305+P351+P338-P310-P264-P280-P302+P352-P321-P332+P313-P362
Risk Statements: 21 · 21/22
Safety Statements: 22 · 22-24/25
WGK Germany: 3 · 3
RTECS: 6300000 · OO6300000
HS Code: 29181980 · 29181980

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 25.3% (66 of 261) of reports.

Danger

H302 (23.4%): Harmful if swallowed [Warning Acute toxicity, oral]；H315 (23.8%): Causes skin irritation [Warning Skin corrosion/irritation]；H318 (72.8%): Causes serious eye damage [Danger Serious eye damage/eye irritation]；H335 (23.4%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

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 261 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 66 of 261 reports by companies.；There are 9 notifications provided by 195 of 261 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 4 items

Chemical: Benzeneacetic acid, .alpha.-hydroxy-

Benzeneacetic acid, .alpha.-hydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzeneacetic acid, .alpha.-hydroxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 01-10-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/19362

Benzeneacetic acid, .alpha.-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Benzeneacetic acid, .alpha.-hydroxy-: Human health tier I assessment；IMAP assessments - Benzeneacetic acid, .alpha.-hydroxy-: Environment tier I assessment

Hazards SummaryCauses gastritis and other liver changes in oral lethal-dose studies of rabbits; [RTECS] An irritant; Chronic exposure may cause kidney injury and digestive tract abnormalities; [Fisher Scientific MSDS]

Hazard Classes and Categories · 2 items

Acute Tox. 4 (50.5%)；Skin Irrit. 2 (86.5%)；Eye Dam. 1 (54.1%)；Eye Irrit. 2 (44.1%)；STOT SE 3 (85.6%)

Acute Tox. 4 (23.4%)；Skin Irrit. 2 (23.8%)；Eye Dam. 1 (72.8%)；STOT SE 3 (23.4%)

Safety & protection

Protective Action Criteria (PAC) · 6 items

25 [mg/m3]

270 [mg/m3]

1600 [mg/m3]

25 [mg/m3]

270 [mg/m3]

1600 [mg/m3]

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.

Regulatory information

Regulatory Information · 4 items

Chemical: Benzeneacetic acid, .alpha.-hydroxy-

Benzeneacetic acid, .alpha.-hydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzeneacetic acid, .alpha.-hydroxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 01-10-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/19362

Benzeneacetic acid, .alpha.-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard

Safety data

wgk: 3
rtecs: OO6300000
hs_code: 29181980
risk_code: 21/22
Signal word: Danger
Symbol(GHS): GHS07,GHS05
safety_code: 22-24/25
Hazard statements: H302-H315-H318-H335
Precautionary statements: P264-P270-P301+P312-P330-P501-P280-P305+P351+P338-P310-P264-P280-P302+P352-P321-P332+P313-P362

Chemistry & industry

Pharmacology

ATC Code · 4 items

J - Antiinfectives for systemic use；J01 - Antibacterials for systemic use；J01X - Other antibacterials；J01XX - Other antibacterials；J01XX06 - Mandelic acid

B - Blood and blood forming organs；B05 - Blood substitutes and perfusion solutions；B05C - Irrigating solutions；B05CA - Antiinfectives；B05CA06 - Mandelic acid

QB - Blood and blood forming organs；QB05 - Blood substitutes and perfusion solutions；QB05C - Irrigating solutions；QB05CA - Antiinfectives；QB05CA06 - Mandelic acid

QJ - Antiinfectives for systemic use；QJ01 - Antibacterials for systemic use；QJ01X - Other antibacterials；QJ01XX - Other antibacterials；QJ01XX06 - Mandelic acid

Uses & manufacturing

UsesUsed as a urinary antiseptic; [Merck Index]

U.S. Production2023: 75,000 - <500,000 lb；2022: 75,000 - <500,000 lb；2021: 75,000 - <500,000 lb；2020: <75,000 lb

Industry UsesIntermediate

Use ClassificationCosmetics -> Antimicrobial

General Manufacturing Information · 2 items

All Other Chemical Product and Preparation Manufacturing

Benzeneacetic acid, .alpha.-hydroxy-: ACTIVE

Applications · 2 items

DescriptionDL-Mandelic acid is a chemical compound belonging to the family of alpha hydroxy acids (AHAs). It is a racemic mixture containing equal amounts of the D and L enantiomers of Mandelic acid. It is commonly used in skincare products for its exfoliating and antibacterial properties. DL-Mandelic Acid is useful in suppressing pigmentation, treating inflammatory non-cystic acne, and rejuvenating photoaged skin. Moreover, it has proven useful in preparing the skin for laser peeling and helping the skin heal after laser surgery. This product appears as a white crystal substance.

UsesDL-Mandelic acid is used as a chemical reagent, in organic synthesis, and as a pharmaceutical raw material and intermediate, dye intermediate, etc.

Upstream & downstream products

Upstream raw materials

Suppliers50 total

Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]

湖北万得化工有限公司15377098680 15377098680 · [email protected]

成都超九八生物科技有限公司13348960310 13348960310 · [email protected]

合肥翰刚医药科技有限公司+8618062405514 · [email protected]

河北创之源生物科技有限公司13012111162

Additional notes · 1 item

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 is functionally related to an acetic acid. It is a conjugate acid of a mandelate.