CAS 579-07-7 1-Phenyl-1,2-propanedione (HCID 11363)

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Basic information

CAS: 579-07-7
Standard SMILES: CC(=O)C(=O)c1ccccc1
InChIKey: BVQVLAIMHVDZEL-UHFFFAOYSA-N
Molecular formula: C9H8O2
Average molar mass: 148.16 g/mol
Monoisotopic mass: 148.0524295

Overview

1-phenyl-1,2-propanedione is an alpha-diketone that consists of 1-phenylpropane bearing keto substituents at positions 1 and 2. It is found in coffee. It has a role as a plant metabolite. It is an alpha-diketone and an aromatic ketone. It derives from a hydride of a propylbenzene.

Names & identifiers

Preferred name: 1-Phenyl-1,2-propanedione
IUPAC: 1-phenylpropane-1,2-dione
English name: 1-Phenyl-1,2-propanedione
Molecular formula: C9H8O2
Molecular weight: 148.16

Names & synonyms

1-PHENYL-1,2-PROPANEDIONE1-Phenylpropane-1,2-dione579-07-7AcetylbenzoylAcetyl benzoylBenzoylacetylPyruvophenone1,2-Propanedione, 1-phenyl-MethylphenylglyoxalBenzoyl methyl ketonePhenylmethyldiketoneMethyl phenyl diketone

Show more names

FEMA 32261-Phenyl-12-propanedione-1,2-propanedione2-Oxopropiophenone

3-Phenyl-2,3-propanedioneMethyl phenyl glyoxalPhenyl methyl diketoneFEMA No. 3226ZB5XA3GD0IDTXSID3060372NSC-7643CHEBI:63552

Database identifiers

CAS: 579-07-7
PubChem CID: 11363
DTXSID: DTXSID3060372
ChEMBL: CHEMBL192258
ChEBI: CHEBI:63552
UNII: ZB5XA3GD0I
EC Number: 209-435-2
Nikkaji: J95.015G

Properties

Computed structural properties

XLogP: 1.7
Topological polar surface area: 34.1 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 2
Heavy atoms: 11
Formal charge: 0
Complexity: 166

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Aromatic Ketones

SpringerMaterials PropertiesSchoenflies notation

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Density · 2 items

1.096-1.116

1.007 @ 20°C/4°C

Flavoring AgentsEU Flavoring substances

Solubility · 3 items

2.6 mg/mL at 20 °C

insoluble in water; soluble in organic solvents, oils

miscible at room temperature (in ethanol)

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 0.8% (11 of 1445) of reports.

Danger

H302 (97.4%): Harmful if swallowed [Warning Acute toxicity, oral]

P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1445 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: 1,2-Propanedione, 1-phenyl-

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

1,2-Propanedione, 1-phenyl-: 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; [JECFA] A skin and strong eye irritant; Harmful by ingestion; [Sigma-Aldrich MSDS] See Acetophenone.

Hazard Classes and CategoriesAcute Tox. 4 (97.4%)

Safety & protection

Protective Action Criteria (PAC) · 3 items

12 [mg/m3]

130 [mg/m3]

790 [mg/m3]

Safety data

PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
tsca

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

UsesUsed as a flavoring agent; [FDA]

Use Classification · 5 items

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information1,2-Propanedione, 1-phenyl-: ACTIVE

Applications · 3 items

OccurrenceReported found as a constituent in coffee, baked potato and butter.

UsesPyruvophenone was used in the synthesis of opioid receptor agonists for gastrointestinal disorders. The enantioselective hydrogenation of Pyruvophenone over Pt colloids was also studied.

General Description1-Phenyl-1,2-propanedione is a volatile flavor compound found in khat leaves and cambará honey.