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
Show more names
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
- Formal charge
- 0
- Complexity
- 123
Experimental & physicochemical properties
Solubility
Practically insoluble or insoluble in water
Soluble (in ethanol)
Physical Description
Other Solid; Liquid
White or off-white powder; [Alfa Aesar MSDS]
White to off-white crystals, chips or chunks; Slight berry to sweet balsam aroma
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)
- FEMA
- 4330 · 4330 | 4-HYDROXYACETOPHENONE
- Flash point
- 166 °C · 166 °C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 0.1 g/mL, · methanol: 0.1 g/mL, clear
- form
- Crystalline Powder
- pka
- 8.05 · 8.05(at 25℃)
- color
- Almost white to beige
- Specific Gravity
- 1.109 · 1.109
- Odor
- 10 % · at 10.00 % in dipropylene glycol. mild sweet hawthorn balsam mimosa
- Odor Type
- floral
- Water Solubility
- 10 g/L · 10 g/L (22 ºC)
- JECFA Number
- 2040 · 2040
- BRN
- 774355 · 774355
- Cosmetics Ingredients Functions
- ANTIOXIDANT
- InChI
- 1S/C8H8O2/c1-6(9)7-2-4-8(10)5-3-7/h2-5,10H,1H3
- InChIKey
- TXFPEBPIARQUIG-UHFFFAOYSA-N
- SMILES
- CC(=O)c1ccc(O)cc1
- LogP
- 1.35 at · 1.35 at 25℃
- CAS DataBase Reference
- 99 · 99-93-4(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- 4 · 4-HYDROXYACETOPHENONE
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 1 L3HT4CMH · G1L3HT4CMH
- NIST Chemistry Reference
- 4 · Acetophenone, 4'-hydroxy-(99-93-4)
- EPA Substance Registry System
- 4 · 4-Hydroxyacetophenone (99-93-4)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 319 · H319-H412
- Precautionary statements
- 264 · P264-P273-P280-P305+P351+P338-P337+P313-P501
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 36 · 36/37/38-22
- Safety Statements
- 26 · 26-36/37-37/39-24/25-22-36
- WGK Germany
- 3 · 3
- RTECS
- 4959775 · PC4959775
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29145000 · 29145000
- Storage Class
- 13 · 13 - Non Combustible Solids
- Hazard Classifications
- 3 Eye · Aquatic Chronic 3Eye Irrit. 2
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
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
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
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
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 26-36/37-37/39-24/25-22-36
- Storage Class
- 13 - Non Combustible Solids
- Hazard statements
- H319-H412
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Chronic 3Eye Irrit. 2
- Precautionary statements
- P264-P273-P280-P305+P351+P338-P337+P313-P501
Chemistry & industry
Pharmacology
Uses & manufacturing
Uses
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]
Use Classification
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
All Other Chemical Product and Preparation Manufacturing
Ethanone, 1-(4-hydroxyphenyl)-: ACTIVE
Applications
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
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°.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Additional notes
DefinitionChEBI: A monohydroxyacetophenone carrying a hydroxy substituent at position 4'.
Related reactions
Compound notes
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