(+-)-3,4-Dihydroxymandelic acid

HCID 85782

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Basic information

CAS: 14883-87-5
Standard SMILES: O=C(O)C(O)c1ccc(O)c(O)c1
InChIKey: RGHMISIYKIHAJW-UHFFFAOYSA-N
Molecular formula: C8H8O5
Average molar mass: 184.15 g/mol
Monoisotopic mass: 184.03717336

Overview

3,4-dihydroxymandelic acid is a catechol that is the 3,4-dihydroxy derivative of mandelic acid; a metabolite of L-dopa. It has a role as an antioxidant, a drug metabolite, a mouse metabolite and a human metabolite. It is a member of catechols and a 2-hydroxy monocarboxylic acid. It is functionally related to a mandelic acid. It is a conjugate acid of a 3,4-dihydroxymandelate.

Names & identifiers

Preferred name: (+-)-3,4-Dihydroxymandelic acid
IUPAC: 2-(3,4-dihydroxyphenyl)-2-hydroxyacetic acid
English name: 3,4-Dihydroxymandelic acid
Molecular formula: C8H8O5
Molecular weight: 184.15

Names & synonyms

3,4-Dihydroxymandelic acid775-01-92-(3,4-dihydroxyphenyl)-2-hydroxyacetic acidDOMAMandelic acid, 3,4-dihydroxy-WDP6VCX5T6DTXSID30862411CHEBI:27637DHMARefChem:905495DTXCID50811183(+-)-3,4-Dihydroxymandelic acid

Show more names

C07470Isoproternol ImpurityAdrenaline Impurity 128Isoprenaline Impurity 35DL-3,4-Dihydroxymandelic Acid >α,3,4-Trihydroxybenzeneacetic acidBenzeneacetic acid, α,3,4-trihydroxy-

212-269-3dl-3,4-Dihydroxymandelic acid14883-87-5Dihydroxymandelic acidrac 3,4-Dihydroxymandelic Acid3,4-Dihydroxymandelate3,4-dihydroxyphenylglycolic acid(+/-)-3,4-Dihydroxymandelic acid

Database identifiers

CAS: 14883-87-5、775-01-9
PubChem CID: 85782
DTXSID: DTXSID30862411
ChEBI: CHEBI:27637
UNII: WDP6VCX5T6
EC Number: 212-269-3、238-956-8
Nikkaji: J128.158E

Properties

Computed structural properties

XLogP: -0.6
Topological polar surface area: 98 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 5
Rotatable bonds: 2
Heavy atoms: 13
Formal charge: 0
Complexity: 193

Experimental & physicochemical properties

Physical DescriptionSolid

Collision Cross Section · 3 items

137.4 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

132 Å² [M+H-H2O]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

137.7 Å² [M-H]-

Physicochemical properties

Melting point: 136 · 136-137 °C (dec.)
Boiling point: 487.5 · 487.5±40.0 °C(Predicted)
Density: 1.644 · 1.644±0.06 g/cm3(Predicted)
storage temp.: -20 °C · -20°C Freezer, Under Inert Atmosphere
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
pka: 3.42 · 3.42±0.10(Predicted)
color: White to Pale Beige
Stability: Light , Temperature and Air Sensitive
FDA UNII: 6 VCX5T6 · WDP6VCX5T6
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319
Precautionary statements: 264 · P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
HS Code: 2918.29 · 2918.29.7500

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

hs_code: 2918.29.7500
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Hazard statements: H315-H319
Precautionary statements: P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313