CAS 2150-46-1 Methyl Gentisate (HCID 75077)

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Basic information

CAS: 2150-46-1
Standard SMILES: COC(=O)c1cc(O)ccc1O
InChIKey: XGDPKUKRQHHZTH-UHFFFAOYSA-N
Molecular formula: C8H8O4
Average molar mass: 168.15 g/mol
Monoisotopic mass: 168.04225873

Names & identifiers

Preferred name: Methyl Gentisate
IUPAC: methyl 2,5-dihydroxybenzoate
English name: Methyl 2,5-dihydroxybenzoate
Molecular formula: C8H8O4
Molecular weight: 168.15

Names & synonyms

Methyl gentisateRefChem:817725Methyl 2,5-dihydroxybenzoate2150-46-12,5-Dihydroxybenzoic acid methyl estermethyl dihydroxybenzoateGentisic Acid Methyl EsterBenzoic acid, 2,5-dihydroxy-, methyl esterGentisic acid, methyl esterMFCD00016464LS28B004KMCHEMBL1978880

Show more names

Methyl GentianaRARECHEM AL BF 0043TIMTEC-BB SBB0077112,5-hydroxybenzoateGentisic acid methylMethyl 2,5-DihydroxybenMETHYL 3,6-DIHYDROXYBENZOATE

NSC-618316methyl2,5-dihydroxybenzoateMethyl 2,?5-?DihydroxybenzoateMethyl-2,5-dihydroxybenzoateMETIL GENTISATOORISTAR MDHB25UNII-LS28B004KMSCHEMBL38890

Database identifiers

CAS: 2150-46-1
PubChem CID: 75077
DTXSID: DTXSID80175841
ChEMBL: CHEMBL1978880
ChEBI: CHEBI:191966
UNII: LS28B004KM
EC Number: 218-427-8
Nikkaji: J80.402I

Properties

Computed structural properties

XLogP: 2.6
Topological polar surface area: 66.8 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 2
Heavy atoms: 12
Formal charge: 0
Complexity: 168

Experimental & physicochemical properties

Physical DescriptionPowder; [Alfa Aesar MSDS]

Kovats Retention Index · 2 items

1519

2993；2985

Physicochemical properties

Melting point: 86 · 86-88 °C (lit.)
Boiling point: 136 °C · 136 °C / 1mmHg
Density: 1.354 · 1.354±0.06 g/cm3(Predicted)
storage temp.: Inert atmosphere,Room Temperature
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
pka: 9.87 · 9.87±0.18(Predicted)
color: Off-White to Pale Beige
Stability: Hygroscopic
Cosmetics Ingredients Functions: CHELATING
InChI: InChI=1S/C8H8O4/c1-12-8(11)6-4-5(9)2-3-7(6)10/h2-4,9-10H,1H3

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 0.7% (1 of 152) of reports.

Danger

H315 (30.3%): Causes skin irritation [Warning Skin corrosion/irritation]；H317 (69.1%): May cause an allergic skin reaction [Warning Sensitization, Skin]；H318 (69.1%): Causes serious eye damage [Danger Serious eye damage/eye irritation]；H319 (30.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (29.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]；H400 (69.1%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 152 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 1 of 152 reports by companies.；There are 8 notifications provided by 151 of 152 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 InformationStatus: Active Update: 17-12-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/21717

Hazards SummaryA skin and strong eye irritant; [Alfa Aesar MSDS] See Methyl benzoate.

Hazard Classes and CategoriesSkin Irrit. 2 (30.3%)；Skin Sens. 1 (69.1%)；Eye Dam. 1 (69.1%)；Eye Irrit. 2 (30.3%)；STOT SE 3 (29.6%)；Aquatic Acute 1 (69.1%)

Chemistry & industry

Applications · 3 items

UsesMethyl 2,5-dihydroxybenzoate (methyl gentisate) may be used as a starting material in the synthesis of euonyminol.

Usesmethyl gentisate is also known as methyl dihydroxybenzoate. It is a skin-lightening ingredient that acts by inhibiting the melanocyte’s production of tyrosinase. It can be naturally obtained from gentian root.

General DescriptionMethyl 2,5-dihydroxybenzoate (methyl gentisate) is an alkyl ester of gentisic acid. It is reported to show less cytotoxic and mutagenic activity than hydroquinone with a potential to inhibit melanogenesis. It has been synthesized from 2,5-dihydroxybenzoic acid. The crystal structure of the molecule was found to be planar.