Basic information
- Standard SMILES
CC(=O)CO- InChIKey
XLSMFKSTNGKWQX-UHFFFAOYSA-N- Molecular formula
- C3H6O2
- Average molar mass
- 74.08 g/mol
- Monoisotopic mass
- 74.03677943
Overview
Hydroxyacetone is a propanone that is acetone in which one of the methyl hydrogens is replaced by a hydroxy group. It has a role as a mouse metabolite, an Escherichia coli metabolite and a human metabolite. It is a primary alpha-hydroxy ketone, a primary alcohol, a member of propanones and a methyl ketone. It is functionally related to an acetone.
Names & identifiers
- Preferred name
- Hydroxyacetone
- IUPAC
- 1-hydroxypropan-2-one
- English name
- Hydroxyacetone
- Molecular formula
- C3H6O2
- Molecular weight
- 74.08
Names & synonyms
Hydroxyacetone116-09-6Acetol1-hydroxypropan-2-oneAcetone alcohol2-Propanone, 1-hydroxy-1-Hydroxy-2-propanone1-HydroxyacetoneACETYLCARBINOLAcetylmethanol2-OxopropanolPyruvic alcohol
Show more names
1-hydroxy-propan-2-oneHydroxyacetonHydroxypropanoneMONOHYDROXYACETONE
Hydroxy-2-propanonePyruvinalcoholHydroxymethyl methyl ketone2-Ketopropyl alcohol7I7YM0835WNSC-102497DTXSID8051590CHEBI:27957
Database identifiers
- CAS
116-09-6- PubChem CID
- 8299
- DTXSID
DTXSID8051590- ChEBI
CHEBI:27957- UNII
- 7I7YM0835W
- EC Number
- 204-124-8
- Nikkaji
- J2.470H
Properties
Computed structural properties
- XLogP
- -0.7
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 5
- Formal charge
- 0
- Complexity
- 40.2
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Other Organic Compounds
SpringerMaterials PropertiesSchoenflies notation
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density
1.079-1.085 (20 °C)
1.082 @ 20°C
Flavoring AgentsEU Flavoring substances
Solubility
1.00E+06 mg/L @ 20 °C (exp)
Soluble in water
Soluble (in ethanol)
Boiling Point
145.00 to 146.00 °C. @ 760.00 mm Hg
145-146 °C
146 °C @760 [mm Hg]
Melting Point
-17 °C
-17 °C
Vapor Pressure
2.95 [mmHg]
2.2 [mm Hg] @20 °C
Refractive Index1.419-1.430
Physical Description
Colorless liquid with a peculiar odor; [Merck Index] Clear light yellow liquid; [Aldrich MSDS]
Liquid
Clear colourless to yellow liquid; Pungent, sweet-caramellic, somewhat choking etheral aroma
Physicochemical properties
- Melting point
- -17 °C · -17 °C (lit.)
- Boiling point
- 145 · 145-146 °C (lit.)
- Density
- 1.082 g/mL · 1.082 g/mL at 25 °C (lit.)
- vapor pressure
- 9.01 hPa · 9.01hPa at 25℃
- FLAVIS Number
- 7.169 · 07.169 | 1-Hydroxypropan-2-one
- refractive index
- 20 · n20/D 1.425(lit.)
- FEMA
- 4462 · 4462 | HYDROXYACETONE
- Flash point
- 133 °F · 133 °F
- storage temp.
- 2 · 2-8°C
- solubility
- water: miscible
- pka
- 13.14 · 13.14±0.10(Predicted)
- form
- clear liquid
- color
- Colorless liquid
- Specific Gravity
- 1.09 · 1.090 (20/4℃)
- Odor
- 10 % · at 10.00 % in dipropylene glycol. pungent sweet caramellic ethereal
- Odor Type
- caramellic
- Water Solubility
- Miscible with water, alcohol and ether.
- Sensitive
- Hygroscopic
- Merck
- 14 · 14,65
- JECFA Number
- 1945 · 1945
- BRN
- 605368 · 605368
- Henry's Law Constant
- 7.7 · 7.7×101 mol/(m3Pa) at 25℃, Lee and Zhou (1993)
- Stability
- Stable. Flammable. Incompatible with strong oxidizing agents, strong acids. Protect from moisture - hygroscopic.
- InChI
- 1S/C3H6O2/c1-3(5)2-4/h4H,2H2,1H3
- InChIKey
- XLSMFKSTNGKWQX-UHFFFAOYSA-N
- SMILES
- CC(=O)CO
- LogP
- 0.3 at · 0.3 at 25℃
- Substances Added to Food (formerly EAFUS)
- HYDROXYACETONE
- CAS DataBase Reference
- 116 · 116-09-6(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 7 I7YM0835W · 7I7YM0835W
- NIST Chemistry Reference
- 2 · 2-Propanone, 1-hydroxy-(116-09-6)
- EPA Substance Registry System
- 1 · 1-Hydroxyacetone (116-09-6)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02
- Signal word
- Warning
- Hazard statements
- 226 · H226
- Precautionary statements
- 210 · P210-P233-P240-P241-P242-P243
- PPE
- Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
- Risk Statements
- 2017 · 2017/10/16
- Safety Statements
- 23 · 23-24/25-5
- RIDADR
- 1224 · UN 1224 3/PG 3
- WGK Germany
- 1 · 1
- RTECS
- 2800000 · UC2800000
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- III
- HS Code
- 29144090 · 29144090
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 3 Muta · Flam. Liq. 3Muta. 2
- Toxicity
- 500 mg/plate · mmo-sat 500 mg/plate ABCHA6 47,2461,83
- REACH Registrations
- Active
- Limited Quantities
- 5 L · 5.0 L (1.3 gallons) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 34.9% (114 of 327) of reports.
Warning
H226 (65.1%): Flammable liquid and vapor [Warning Flammable liquids]
P203, P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P318, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 327 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 2-Propanone, 1-hydroxy-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Status: Active Update: 09-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/27189
Acetone alcohol: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryMay cause irritation; [Aldrich MSDS]
Hazard Classes and CategoriesFlam. Liq. 3 (65.1%)
Safety & protection
Protective Action Criteria (PAC)
6.0 [mg/m3]
66 [mg/m3]
400 [mg/m3]
Safety data
- PPE
- Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- UC2800000
- ridadr
- UN 1224 3/PG 3
- hs_code
- 29144090
- Toxicity
- mmo-sat 500 mg/plate ABCHA6 47,2461,83
- risk_code
- 2017/10/16
- Signal word
- Warning
- Symbol(GHS)
- GHS02
- safety_code
- 23-24/25-5
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- III
- Hazard statements
- H226
- Limited Quantities
- 5.0 L (1.3 gallons) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Flam. Liq. 3Muta. 2
- Precautionary statements
- P210-P233-P240-P241-P242-P243
Chemistry & industry
Uses & manufacturing
UsesUsed in organic synthesis (reagent) and peptide synthesis (protecting group); [Merck Index] Used as a solvent for nitrocellulose; [Hawley]
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
General Manufacturing Information2-Propanone, 1-hydroxy-: ACTIVE
Applications
UsesHydroxyacetone is a chemical reagent used in various organic chemical reactions. It is a component of the Mannich reaction, amino acid caalyzes direct asymmetric aldol reactions. In the pharmaceutical setting, this compound is used in the synthesis of imidazoles acting as potent and orally active antihypertensive agents. It is also used in the syntheses of 2-oxo-propionaldehyde, imidazoles, polyols, acrolein, dyes and skin tanning agents. It yields (R)-1,2-propanediol upon reduction of hydroxyacetone in the presence of a microbial cell catalyst.
General DescriptionHydroxyacetone (Acetol) is important for the manufacture of polyols, acrolein, dyes and skin tanning agents. It undergoes asymmetric reduction to yield (R)-1,2-propanediol in the presence of microbial cell catalyst.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: A propanone that is acetone in which one of the methyl hydrogens is replaced by a hydroxy group.
Related reactions
82 records
Linked notes
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