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1-benzoyl acetone

1-benzoyl acetone is a diketone compound known for its balsamic odor, used primarily in flavor and fragrance applications.
Chemical Structure

General Material Description

1-benzoyl acetone, also known as benzoylacetone or acetoacetophenone, is a diketone organic compound with the molecular formula C10H10O2. It typically appears as a crystalline solid with a melting point between 56 and 58°C. The compound displays a characteristic balsamic odor with nuances of acetophenone balsam, woody, dry opoponax, and vanilla notes according to sensory evaluations at a 1.00% concentration or lower. It is a key intermediate in synthetic chemistry and is employed for its distinct aroma in flavor and fragrance formulations. Its structure links closely to the 1-phenyl-1,3-butanedione scaffold, as confirmed in authoritative chemical databases such as PubChem. The compound is sourced primarily through chemical synthesis from acetophenone derivatives and is valued for its aromatic qualities.

Occurrence, Applicability & Potential Uses

1-benzoyl acetone is not widely reported in natural biological systems but is synthesized for its use as a fragrance and flavor agent. Its balsamic, amber, opoponax, chypre, heather, oriental, and vanilla odor facets make it versatile in perfumery compositions and flavoring applications. The compound’s use in the fragrance industry complies with IFRA (Global) standards, which recommend maximum usage levels up to 0.7% in fragrance concentrates to ensure safe application. This regulation guides formulators in leveraging its aroma profile while minimizing potential allergenic or irritant effects. Its physicochemical properties also influence its behavior in formulations, contributing to its substantivity and olfactory impact.

Physico-Chemical Properties Summary

1-benzoyl acetone is a moderately lipophilic compound, with an estimated logP of 2.52, indicating its affinity for organic phases and solvents such as alcohol, where it readily dissolves. The compound has limited water solubility, approximately 383 mg/L at 25°C. Its melting point ranges from 56 to 58°C, and it exhibits a high boiling point near 261 to 262°C at atmospheric pressure. Vapor pressure at 25°C is low, around 0.011 mmHg, indicating low volatility under ambient conditions. The flash point, measured by the Tag Closed Cup method, is approximately 206°F (about 96.7°C), denoting moderate flammability. These properties are integral for formulation scientists considering volatility, solubility, and thermal stability in flavor and fragrance products. The molecule’s diketone structure contributes to its chemical reactivity and odor profile.

FAQ

What is 1-benzoyl acetone and what are its main characteristics?
1-benzoyl acetone is an organic diketone compound with the molecular formula C10H10O2. Also known by synonyms such as benzoylacetone and acetoacetophenone, it exhibits a distinctive balsamic and woody odor profile used primarily in flavor and fragrance applications. It is a crystalline solid with moderate melting and boiling points and possesses moderate solubility in alcohol but limited water solubility.
Where is 1-benzoyl acetone typically used and how is it applied in industry?
This compound is used mainly in the flavor and fragrance industries as an aroma ingredient contributing balsamic, amber, and vanilla notes. Its usage levels are regulated to ensure safety and optimal sensory effect. It is synthesized chemically and incorporated into perfume and flavor formulations, benefiting from its moderate lipophilicity and stability under typical formulation conditions.
What safety and regulatory considerations apply to 1-benzoyl acetone?
1-benzoyl acetone has no significant hazard classification under OSHA or GHS standards and is generally regarded as safe for use within recommended limits. IFRA (Global) guidelines recommend a maximum usage concentration of 0.7% in fragrance concentrates to minimize potential sensitization. Precautionary measures include avoiding inhalation of vapors and contact with skin or eyes. The compound is listed under REACH (EU) with EINECS number 202-286-4, and regulatory compliance is crucial for industry applications.

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

1-phenylbutane-1,3-dione
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):7166
Pubchem (sid):134970794
Publications by PubMed
Car-Parrinello and path integral molecular dynamics study of the intramolecular hydrogen bonds in the crystals of benzoylacetone and dideuterobenzoylacetone.
Tautomeric and conformational properties of benzoylacetone, CH3-C(O)-CH2-C(O)-C6H5: gas-phase electron diffraction and quantum chemical study.
Absorption spectroscopic study of synergistic extraction of praseodymium with benzoyl acetone in presence of crown ether.
Monitoring ultrafast intramolecular proton transfer processes in an unsymmetric β-diketone.
The low-barrier hydrogen bond of deuterated benzoylacetone probed by very low temperature neutron and X-ray diffraction studies and theoretical calculations.
X-ray and neutron diffraction study of benzoylacetone in the temperature range 8-300 K: comparison with other cis-enol molecules.
The sensitive determination of nucleic acids using fluorescence enhancement of Eu3+-benzoylacetone-cetyltrimethylammonium bromide-nucleic acid system.
Potential anticonvulsants IV: Condensation of isatin with benzoylacetone and isopropyl methyl ketone.
Metal chelates of azo-pyridazine dyes Chelating tendencies of benzoylacetone-monohydrazone-3-hydrazino-4-benzyl-6-phenylpyridazine (bahp).
Solution and solid state structure and tautomerism of azo coupled enaminone derivatives of benzoylacetone.
1,5-Dimethyl-4-(1-methyl-3-oxo-3-phenylprop-1-enyl-amino)-2-phenyl-1H-pyrazol-3(2H)-one.
Friedel-Crafts Coupling of Electron-Deficient Benzoylacetones Tuned by Remote Electronic Effects.
Photoresist-free fully self-patterned transparent amorphous oxide thin-film transistors obtained by sol-gel process.
Mono- and binuclear copper(II) complexes of new hydrazone ligands derived from 4,6-diacetylresorcinol: Synthesis, spectral studies and antimicrobial activity.
Synthesis of Pyrroloquinones via a CAN Mediated Oxidative Free Radical Reaction of 1,3-Dicarbonyl Compounds with Aminoquinones.
Synthesis, spectral characterization, and antiproliferative studies of mixed ligand titanium complexes of adamantylamine.
Highly selective synergism for the extraction of lanthanoid(III) ions with β-diketones and trioctylphosphine oxide in an ionic liquid.
Conformational analysis, intramolecular hydrogen bonding, and vibrational assignment of 4,4-dimethyl-1-phenylpentane-1,3-dione.
Low-temperature metal-oxide thin-film transistors formed by directly photopatternable and combustible solution synthesis.
Phosphomolybdic and phosphotungstic acids as efficient catalysts for the synthesis of bridged 1,2,4,5-tetraoxanes from β-diketones and hydrogen peroxide.
Spectroscopic investigations of nano-sized titanium(IV) complexes containing electron-rich oxygen-based ligands.
New tetradentate Schiff bases of 2,2-dimethyl-1,3-diaminopropane and acetylacetone derivatives and their vanadyl complexes.
Synthesis and spectral characterization of ternary mixed-vanadyl β-diketonate complexes with Schiff bases.
Portable formaldehyde monitoring device using porous glass sensor and its applications in indoor air quality studies.
Volatile oil composition of Pogostemon heyneanus and comparison of its composition with patchouli oil.
Gold(III) N-heterocyclic carbene complexes mediated synthesis of β-enaminones from 1,3-dicarbonyl compounds and aliphatic amines.
Dithiocarbazate complexes with the [M(PPh3)]2+ (M = Pd or Pt) moiety: synthesis, characterization and anti-Trypanosoma cruzi activity.
Inhibition by diacylmethane derivatives of mutagenicity in Salmonella typhimurium and tRNA-binding of chemical carcinogens.
[Synthesis and luminescence properties of europium (III) complexes].
Four new dinuclear Cu(ii) hydrazone complexes using various organic spacers: syntheses, crystal structures, DNA binding and cleavage studies and selective cell inhibitory effect towards leukemic and normal lymphocytes.
Vibrational assignment and structure of dibenzoylmethane. A density functional theoretical study.
On the electronic nature of low-barrier hydrogen bonds in enzymatic reactions.
Inhibition by diacylmethane derivatives of mutagenicity and nucleic acid binding of 2-aminofluorene derivatives.
Vibrational assignment and structure of trifluorobenzoylacetone. A density functional theoretical study.
Spectral and thermal studies of some chromium and molybdenum complexes with ONO donor Schiff bases.
Individual and simultaneous spectrophotometric determination of dapsone and metoclopramide HCl in pharmaceutical dosage forms and synthetic binary mixtures.
Single-drop microextraction combined with low-temperature electrothermal vaporization ICPMS for the determination of trace Be, Co, Pd, and Cd in biological samples.
Synthesis of some novel pyrazolo[3,4-b]pyridine and pyrazolo[3,4-d]pyrimidine derivatives bearing 5,6-diphenyl-1,2,4-triazine moiety as potential antimicrobial agents.
Synthesis and molluscicidal activity of some new thiophene, thiadiazole and pyrazole derivatives.
Functional characterization of an orphan cupin protein from Burkholderia xenovorans reveals a mononuclear nonheme Fe2+-dependent oxygenase that cleaves beta-diketones.
Synthesis and structural characterization of nonanuclear lanthanide complexes.
Synthesis and structural characterization of a novel dinuclear complex compound formed by the aerial oxidation of cobalt(II) having an interligand C-C sigma-bond.
Comparison of copper speciation in coastal marine waters measured using analytical voltammetry and diffusion gradient in thin-film techniques.
Synthesis of novel heterocycles through reaction of indolin-2-one derivatives with active methylene and amino reagents.
Improved luminescence properties of europium complexes encapsulated into mesoporous SBA-15.
Diffraction gratings of photosensitive ZrO2 gel films fabricated with the two-ultraviolet-beam interference method.
Intramolecular hydrogen bonding (proton transfer) of 1-phenyl-1,3-butanedione.
Intramolecular rearrangement for regioselective complexation by intramolecular CH/pi interaction in a hydrophobic cavity of a ruthenium coordination sphere.
The charge density distribution in a model compound of the catalytic triad in serine proteases.
Strong copper-binding behavior of terrestrial humic substances in seawater.
Synthesis and evaluation of technetium-99m monocationic mixed ligand complexes of phenyl substituted/condensed tetradentate Schiff's bases and trimethylphosphine.
Antiviral compounds. 1. Structure-activity relationship of some antiviral enediones derived from aldehydo sugars.
Synthesis and pharmacological activity of some 2,3-dihydrofuran-2,3-dione derivatives.
Synthesis and pharmacological studies of 2'-sulphonyl[3-(3H-2,4-disubstituted-1,5-benzodiazepino)]-2,5-dimethyl-6,7-benzomorphans.
Tautomerization equilibria in aqueous micellar solutions: a spectrophotometric and factor-analytical study.
Evaluation of the cytotoxic and pro-apoptotic activities of Eu(III) complexes with appended DNA intercalators in a panel of human malignant cell lines.
Synthesis and anxiolytic activity of 1-phenyl-2-(4-aryl-1,3,4,5-tetrahydropyrido[2,3-b][1 ,4]diazepin-2-ylidene)-ethanone.
Transfer rate of several tris(beta-diketonato)iron(III) complexes at the bulk aqueous--Triton X-100 micellar interface: effects of substituent groups in the extractants.
End-to-end single cyanato and thiocyanato bridged Cu(II) polymers with a new tridentate Schiff base ligand: crystal structure and magnetic properties.
Effect of ligand radicals on vibrational IR, Raman and vibronic spectra of europium beta-diketonates.
Synthesis, characterization, EXAFS investigation and antibacterial activities of new ruthenium(III) complexes containing tetradentate Schiff base.
Preparation of beta-keto esters and beta-diketones by C-acylation/deacetylation of acetoacetic esters and acetonyl ketones with 1-acylbenzotriazoles.
Theoretical study of the symmetry of the (OH...O)- hydrogen bonds in vinyl alcohol-vinyl alcoholate systems.
Reactions of Dimethyl Sulfite with Diorganotin Oxides. One-Pot Synthesis of Methoxydiorganotin Methanesulfonates through the Arbuzov Rearrangement, Spectroscopic Characterization of These Compounds and Their Derivatives, and X-ray Crystal Structures of n-Bu(2)Sn(X)OS(O)(2)Me (X = acac, bzbz, OH).
Synthesis and structural assignment of certain pyrimido[1,2-alpha] benzimidazole derivatives.
Determination of the salting coefficients of benzoyltrifluoroacetone.
Stability constants of lanthanide complexes with salicylhydroxamic acid.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2914.30.0000
ChemSpider:View

General Material Information

Preferred name 1-benzoyl acetone
Trivial Name Benzoylacetone
Short Description 1-phenyl-1,3-butanedione
Formula C10 H10 O2
CAS Number 93-91-4
ECHA Number 202-286-4
FDA UNII I3RUV8U115
Nikkaji Number J4.688D
Beilstein Number 0742413
MDL MFCD00008786
COE Number 11181
Bio Activity Summary External link
NMR Predictor External link
Synonyms
  • acetoacetophenone
  • 2-acetyl acetophenone
  • alpha- acetyl acetophenone
  • acetyl benzoyl methane
  • 2-acetylacetophenone
  • a- acetylacetophenone
  • 1-benzoyl-2-propanone
  • benzoylacetone
  • 1-benzoylacetone
  • 1,3-butanedione, 1-phenyl-
  • 1-phenyl butane-1,3-dione
  • 1-phenyl-1,3-butane dione
  • 1-phenyl-1,3-butanedione
  • 1-phenyl-butane-1,3-dione
  • 1-phenylbutane-1,3-dione
  • 2-propanone, benzoyl-
  • 1-phenylbutane-1,3-dione
  • 1,3-Butanedione, 1-phenyl-
  • 1-Phenyl-1,3-butanedione
  • Acetylbenzoylmethane
  • 2-Propanone, benzoyl-
  • 1-Benzoylacetone
  • 2-Acetylacetophenone
  • 1-Methyl-3-phenyl-1,3-propanedione
  • 1-Benzoyl-2-propanone
  • α-Acetylacetophenone
  • 4-Phenyl-2,4-butanedione
  • NSC 100655
  • NSC 4015
  • NSC 404283
  • NSC 405722
  • NSC 405723
  • NSC 405724
  • NSC 83580
  • NSC 83581
  • NSC 87898
  • NSC 88942
  • NSC 97232
  • NSC 97233
  • 1-Phenylbutan-1,3-dione
  • 4-Oxo-4-phenylbutan-2-one

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 162.18809509277
Melting Point 56 to 58°C @ 760 mm Hg
Boiling Point 261 to 262°C @ 760 mm Hg
Vapor Pressure 0.011 mmHg @ 25 °C
Flash Point TCC Value 96.67 °C TCC
logP (o/w) 2.52 est
Solubility
alcohol Yes
water, 383 mg/L @ 25 °C (exp) Yes
water No

Organoleptic Properties

Odor Type: Balsamic
hawthorn, balsamic, woody, dry, opoponax, vanilla
Odor strength medium , recommend smelling in a 1.00 % solution or less
Substantivity 44 hour(s) at 100.00 %
Luebke, William tgsc, (1984) At 100.00 %. acetophenone balsam woody dry opoponax vanilla

Potential Uses

Applications
Odor purposes Amber , Balsam , Chypre , Heather , Opoponax , Oriental , Vanilla

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 23 - Do not breath vapour.
S 24/25 - Avoid contact with skin and eyes.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD > 500 mg/kg
National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 28, 1953.

unreported-rat LDLo 600 mg/kg
Biochemical Pharmacology. Vol. 14, Pg. 1325, 1965.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for 1-benzoyl acetone usage levels up to:
0.7000 % in the fragrance concentrate.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):93-91-4
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7166
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
1-phenylbutane-1,3-dione
Chemidplus:0000093914
RTECS:EK3540200 for cas# 93-91-4