4'-Hydroxyacetophenone

HCID 7469

Basic information

CAS
99-93-4
Standard SMILES
CC(=O)c1ccc(O)cc1
InChIKey
TXFPEBPIARQUIG-UHFFFAOYSA-N
Molecular formula
C8H8O2
Average molar mass
136.15 g/mol
Monoisotopic mass
136.0524295

Overview

4'-hydroxyacetophenone is a monohydroxyacetophenone carrying a hydroxy substituent at position 4'. It has a role as a mouse metabolite, a plant metabolite and a fungal metabolite.

Names & identifiers

Preferred name
4'-Hydroxyacetophenone
IUPAC
1-(4-hydroxyphenyl)ethanone
English name
4'-Hydroxyacetophenone
Molecular formula
C8H8O2
Molecular weight
136.15

Names & synonyms

4'-Hydroxyacetophenone99-93-44-Hydroxyacetophenone1-(4-Hydroxyphenyl)ethanoneP-HYDROXYACETOPHENONE4-Acetylphenolp-Hydroxyphenyl methyl ketoneEthanone, 1-(4-hydroxyphenyl)-Methyl p-hydroxyphenyl ketonepara-Hydroxyacetophenone(4-Hydroxyphenyl)ethan-1-oneHYDROXYACETOPHENONE, PARA
Show more names
PiceolPOBP-HYDROXYBENZOPHENONEACETYLPHENOLp-Acetylphenolp-Oxyacetophenone
DTXSID0029133G1L3HT4CMHNSC-3698DTXCID209133FEMA NO. 4330CHEBI:28032RefChem:523982CHEBI:24668

Database identifiers

CAS
99-93-4
PubChem CID
7469
DTXSID
DTXSID0029133
ChEMBL
CHEMBL201083
ChEBI
CHEBI:28032
UNII
G1L3HT4CMH
EC Number
202-802-8
Nikkaji
J2.233.995H、J4.976J

Properties

Computed structural properties

XLogP
1.4
Topological polar surface area
37.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
10

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Aromatic Ketones
CosmeticsCosmetic ingredients (Hydroxyacetophenone) -> CIR (Cosmetic Ingredient Review)
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
FragrancesFragrance Ingredient (4-Hydroxyacetophenone) -> IFRA transparency List
LogP1.45
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Physicochemical properties

Melting point
132 · 132-135 °C(lit.)
Boiling point
147 · 147-148 °C3 mm Hg(lit.)
Density
1.109 · 1.109
vapor pressure
0.002 Pa · 0.002Pa at 20℃
FLAVIS Number
7.243 · 07.243 | 4-Hydroxyacetophenone
refractive index
1.5577 · 1.5577 (estimate)

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 3.9% (11 of 279) of reports.

Warning

H302 (45.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 279 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 5 items

Chemical: Ethanone, 1-(4-hydroxyphenyl)-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Ethanone, 1-(4-hydroxyphenyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanone, 1-(4-hydroxyphenyl)- 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: 12-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/11354

Ethanone, 1-(4-hydroxyphenyl)-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummarySafe when used as a flavoring agent in food; [EFSA] A skin and strong eye irritant; Toxic by ingestion; [Alfa Aesar MSDS] See 2'-Hydroxyacetophenone, 3'-Hydroxyacetophenone, and Acetophenone.
EPA Safer ChemicalChemical: 4-Hydroxyacetophenone
Hazard Classes and CategoriesAcute Tox. 4 (45.2%)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
PC4959775
hs_code
29145000
risk_code
36/37/38-22

Chemistry & industry

Pharmacology

Metabolism/Metabolites4-Hydroxyacetophenone has known human metabolites that include (2S,3S,4S,5R)-6-(4-acetylphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid.

Uses & manufacturing

Uses · 2 items

CIR ingredient: Hydroxyacetophenone

A flavoring agent that naturally occurs in cloudberry, coffee, mango, sherry, and in trace amounts in cranberry; [EFSA] Used as an intermediate for plastics, cosmetics, and pharmaceuticals; [ECHA REACH Registrations]

U.S. Production2023: 1,000,000 - <5,000,000 lb
Consumer UsesAntioxidant
Industry UsesAntioxidant
Use Classification · 5 items

EPA Safer Chemical Functional Use Classes -> Preservatives and Antioxidants

Safer Chemical Classes -> Yellow triangle - The chemical has met Safer Choice Criteria for its functional ingredient-class, but has some hazard profile issues

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing Information · 2 items

All Other Chemical Product and Preparation Manufacturing

Ethanone, 1-(4-hydroxyphenyl)-: ACTIVE

Applications · 5 items

OccurrenceReported found in cloudberry, coffee, cranberry, mango, sherry, and wort.

Uses4′-Hydroxyacetophenone has been used as ketone component in the preparation of 1-aryl-3-phenethylamino-1-propanone hydrochlorides, potential cytotoxic agents, via Mannich reactions.

Usesp-Hydroxyacetophenone is widely used in medicine, cosmetics and industrial fields. It is a natural plant extract, which naturally exists in the stems and leaves of the Compositae plant, Artemisia annua, the roots of plants such as Artemisia annua, Rhododendron, and Panax ginseng. It has a good effect on yellow eyes caused by diseases such as hepatitis, and also has a good auxiliary effect on yellow eyes caused by various reasons. Due to its weak molecular activity, high temperature resistance, melting point of 95-97 °C and boiling point of 296 °C, it is widely used in various liquid pharmaceuticals and can prolong the shelf life of other active ingredients under high temperature conditions. It has no harm to human skin and is the safest high-temperature auxiliary active stabilizer in the pharmaceutical industry.

Uses4-Hydroxyacetophenone has been used as ketone component in the preparation of 1-aryl-3-phenethylamino-1-propanone hydrochlorides, potential cytotoxic agents, via Mannich reactions.

General DescriptionPharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards

Preparation methods · 1 item

PreparationPreparation by Fries rearrangement of phenyl acetate with Lewis acidsaluminium chloridein nitrobenzene at 20–25° or at 50–60°in chlorobenzene between 45° and 65°, sealed tube and subjected to high power microwave irradiation for 2 min only (36%) in nitroethane at 60° (44%)in carbon disulfide at 45° (40%)in petroleum ether at 50° (20%) but between 130° and 175° (40–60%)aluminium chloride–sodium chloride mixture at 240–250° (10%) boron trifluoride at 90° (56%) scandium tris(trifluoromethanesulfonate), in nitromethane, at 50° (39%)titanium tetrachloride at 90–100° (34%)ferric chloride at 65° (25%)zinc chloride at 125° (8%) hydrofluoric acid, between 20° and 100° (94%) polyphosphoric acid, between 20° and 100° (69%) (50–53%)(44%)Nafion-XR 500, sulfonic acid type at 100°ZSM-5, in sulfolane, at 180° (28%)H-ZSM-5 at 400° or at 210° (6%) H-Nu-2 at 170° (15%)HY (Si/Al = 3) or fluorided alumina (Al2O3-F; 3 % wt. F), at 400°.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
河北立业化学制品有限公司0310-6697998 13930001710 · [email protected]

Additional notes

DefinitionChEBI: A monohydroxyacetophenone carrying a hydroxy substituent at position 4'.

Related reactions

533 records

Compound notes

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