Mandelic Acid (HCID 1292)

名称と識別子

優先名称: Mandelic Acid
IUPAC: 2-hydroxy-2-phenylacetic acid
現地名: rac-(R*)-α-ヒドロキシベンゼン酢酸
英語名: DL-Mandelic acid
分子式: C8H8O3
分子量: 152.15

名称と別名

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

名称をさらに表示

(±)-マンデル酸rac-(R*)-2-フェニルグリコール酸rac-(R*)-α-ヒドロキシベンゼン酢酸rac-(αR*)-α-ヒドロキシベンゼン酢酸rac-(R*)-2-ヒドロキシ-2-フェニル酢酸DL-アミグダリン酸rac-(R*)-フェニルヒドロキシ酢酸DL-マンデル酸rac-(R*)-ヒドロキシフェニル酢酸rac-(S*)-α-ヒドロキシベンゼン酢酸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

データベース識別子

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

物性

構造計算による物性

XLogP: 0.6
極性表面積: 57.5 Å²
水素結合供与体数: 2
水素結合受容体数: 3
回転可能結合数: 2
重原子数: 11
形式電荷: 0
複雑度: 138

実験および物理化学的性質

Density · 2 件

1.3 @25 °C

Boiling Point320 °C @760 [mm Hg]

Melting Point119 °C

Vapor Pressure0.0000164 [mmHg]

Physical Description · 2 件

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

物理化学的性質

融点: 119 · 119-121 °C(lit.)
沸点: 234.6 °C · 234.6°C (rough estimate)
比重(密度): 1.289 · 1.2890
屈折率: 1.4945 · 1.4945 (estimate)
酸解離定数(Pka): 3.85 · 3.85(at 25℃)
水溶解度: 172.5 g/L · 172.5g/L(24℃)
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 データベース: 611 · 611-72-3(CAS DataBase Reference)
NISTの化学物質情報: Benzeneacetic acid, «alpha»-hydroxy-, (.+/-.)-(611-72-3)

安全と法規制

GHS分類

GHS Classification · 6 件

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.

危険有害性情報

Regulatory Information · 4 件

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 件

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%)

安全と保護具

Protective Action Criteria (PAC) · 6 件

25 [mg/m3]

270 [mg/m3]

1600 [mg/m3]

25 [mg/m3]

270 [mg/m3]

1600 [mg/m3]

毒性情報

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.

法規制情報

Regulatory Information · 4 件

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

安全データ

wgk: 3
rtecs: OO6300000
hs_code: 29181980
risk_code: 21/22
safety_code: 22-24/25

化学と産業

薬理情報

ATC Code · 4 件

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

用途と製造

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 件

All Other Chemical Product and Preparation Manufacturing

Benzeneacetic acid, .alpha.-hydroxy-: ACTIVE

応用分野 · 1 件

説明DL-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.