2-Acetylhydroquinone (HCID 10279)

Names & identifiers

Preferred name: 2-Acetylhydroquinone
IUPAC: 1-(2,5-dihydroxyphenyl)ethanone
English name: 2',5'-Dihydroxyacetophenone
Molecular formula: C8H8O3
Molecular weight: 152.15

Names & synonyms

490-78-81-(2,5-Dihydroxyphenyl)ethanone2',5'-DIHYDROXYACETOPHENONE2-AcetylhydroquinoneQuinacetophenoneAcetylhydroquinone1-(2,5-dihydroxyphenyl)ethan-1-oneEthanone, 1-(2,5-dihydroxyphenyl)-AcetylquinolAcetophenone, 2',5'-dihydroxy-1-Acetyl-2,5-dihydroxybenzene2,5-Dihydroxy-1-acetylbenzene

Show more names

2,5-DIHYDROXYACETOPHENONE2,5-DHAP2-hydroxy-1-(3-hydroxyphenyl)ethan-1-one2,5-Dihydroxyphenyl methyl ketone, 2-Acetyl-1,4-dihydroxybenzene, 2-Acetylhydroquinone, Acetylquinol, Quinacetophenone

NSC 3759EINECS 207-716-4K1H7QH11ZHBRN 0637903AI3-18221NSC-3759DTXSID90600772-ACETYL-1,4-BENZENEDIOL

Database identifiers

CAS: 490-78-8
PubChem CID: 10279
DTXSID: DTXSID9060077
ChEMBL: CHEMBL2348532
ChEBI: CHEBI:173647
UNII: K1H7QH11ZH
EC Number: 207-716-4
Nikkaji: J6.045C

Properties

Computed structural properties

XLogP: 1.7
Topological polar surface area: 57.5 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 1
Heavy atoms: 11
Formal charge: 0
Complexity: 155

Experimental & physicochemical properties

Melting Point202 - 203 °C

Physical DescriptionSolid

Kovats Retention Index2162

Physicochemical properties

Melting point: 204 · 204-206 °C(lit.)
Boiling point: 234.6 °C · 234.6°C (rough estimate)
Density: 1.2143 · 1.2143 (rough estimate)
refractive index: 1.4447 · 1.4447 (estimate)
storage temp.: 30 °C · Store below +30°C.
solubility: 50 mg/mL, · dioxane: 50 mg/mL, clear
pka: 9.86 · 9.86±0.18(Predicted)
form: Crystals or Crystalline Powder
color: Yellow to yellow-green
Water Solubility: insoluble
BRN: 637903 · 637903
Cosmetics Ingredients Functions: SKIN CONDITIONINGBLEACHINGANTIOXIDANT
InChI: 1S/C8H8O3/c1-5(9)7-4-6(10)2-3-8(7)11/h2-4,10-11H,1H3
InChIKey: WLDWSGZHNBANIO-UHFFFAOYSA-N
SMILES: CC(=O)c1cc(O)ccc1O
LogP: 1.274 · 1.274 (est)
CAS DataBase Reference: 490 · 490-78-8(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 1 H7QH11ZH · K1H7QH11ZH
NIST Chemistry Reference: 1 · Ethanone, 1-(2,5-dihydroxyphenyl)-(490-78-8)
EPA Substance Registry System: 1 · Ethanone, 1-(2,5-dihydroxyphenyl)- (490-78-8)
UNSPSC Code: 12352115 · 12352115
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 264 · P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a
target organs: Respiratory system
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
WGK Germany: 3 · 3
RTECS: 7700000 · AM7700000
Hazard Note: Irritant
TSCA: TSCA listed
HS Code: 29145000 · 29145000
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (98%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract 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 50 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；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 InformationEthanone, 1-(2,5-dihydroxyphenyl)-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesSkin Irrit. 2 (100%)；Eye Irrit. 2 (100%)；STOT SE 3 (98%)

Regulatory information

Regulatory InformationEthanone, 1-(2,5-dihydroxyphenyl)-: Does not have an individual approval but may be used under an appropriate group standard

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
tsca: TSCA listed
rtecs: AM7700000
hs_code: 29145000
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
hazard_note: Irritant
safety_code: 26-36
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm；Extracellular

Uses & manufacturing

UsesSynthetic Polymer MALDI Matrix Compounds

General Manufacturing InformationEthanone, 1-(2,5-dihydroxyphenyl)-: ACTIVE

Applications · 3 items

Description2',5'-Dihydroxyacetophenone is a natural phenolic compound that is found in many plants. It has been shown to have anti-inflammatory properties through its ability to inhibit the production of pro-inflammatory cytokines, such as tumor necrosis factor alpha and interleukin 1 beta.

Uses1-(2,5-Dihydroxyphenyl)ethanone is an intermediate used in various synthetic preparations of pharmaceutical goods, 1-(2,5-Dihydroxyphenyl)ethanone was untilized in the synthesis of new flavonoid fatty acid esters with anti-adipogenic and glucose consumption enhancing activities.

Uses2',5'-Dihydroxyacetophenone is an intermediate used in various synthetic preparations of pharmaceutical goods, 1-(2,5-Dihydroxyphenyl)ethanone was untilized in the synthesis of new flavonoid fatty acid esters with anti-adipogenic and glucose consumption enhancing activities.

Preparation methods

PreparationPreparation by Fries rearrangement of hydroquinone diacetate,with aluminium chloride(91%) (76%)(63–77%) (55–60%)with zinc chloride in refluxing acetic acid (quantitative yield)with boron trifluoride etherate in benzene at reflux (65%).