Basic information
- Standard SMILES
O=C(c1ccccc1)C(O)c1ccccc1- InChIKey
ISAOCJYIOMOJEB-UHFFFAOYSA-N- Molecular formula
- C14H12O2
- Average molar mass
- 212.24 g/mol
- Monoisotopic mass
- 212.08372962
Overview
Benzoin is an off-white to yellow-white crystalline solid with an odor of camphor. Slightly acrid taste. When broken the fresh surfaces have a milky-white color. (NTP, 1992)
Names & identifiers
- Preferred name
- Benzoin
- IUPAC
- 2-hydroxy-1,2-diphenylethanone
- English name
- Benzoin
- Molecular formula
- C14H12O2
- Molecular weight
- 212.24
Names & synonyms
BENZOIN119-53-92-Hydroxy-1,2-diphenylethanone2-Hydroxy-2-phenylacetophenoneBenzoylphenylcarbinolDL-BENZOINEthanone, 2-hydroxy-1,2-diphenyl-(+-)-BenzoinPhenylbenzoyl carbinolalpha-Hydroxy-alpha-phenylacetophenonealpha-Hydroxybenzyl phenyl ketoneAerozoin
Show more names
FEMA 2132BENZOIN SUMATRABenzoin, 99.5%Benzoin, ARBENZOIN GUMBENZOIN GUM SIAMA-HYDROXYBENZYL PHENYL KETONEA-HYDROXY-A-PHENYLACETOPHENONE
desyl alcoholPhenyl-alpha-hydroxybenzyl ketoneFEMA No. 2132NCI-C50011(RS)-BenzoinHydroxy-2-phenyl acetophenoneWy 42956DTXSID1020144
Database identifiers
- CAS
119-53-9、579-44-2、8050-35-9、9000-05-9- PubChem CID
- 8400
- DTXSID
DTXSID1020144- ChEMBL
CHEMBL190677- ChEBI
CHEBI:17682- UNII
- L7J6A1NE81
- EC Number
- 204-331-3、209-441-5
- Nikkaji
- J20.621K
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 225
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Other Aromatic Compounds
LogP2.130
OdorSWEET NON-DESCRIPT ODOR
TasteSWEET NON-DESCRIPT TASTE
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density
1.31 at 68 °F (NTP, 1992) - Denser than water; will sink
1.31 g/cm³
Flavoring AgentsEU Flavoring substances
Color/Form
PALE YELLOW CRYSTALS
WHITE CRYSTALS
Solubility
less than 0.1 mg/mL at 64 °F (NTP, 1992)
SOL IN 3335 PARTS WATER, MORE SOL IN HOT WATER; SOL IN 5 PARTS PYRIDINE; ACETONE; SOL IN BOILING ALC; SLIGHTLY SOL IN ETHER /DL-FORM/
SOL IN HOT METHANOL; SOL IN HOT ALCOHOL; ACETONE /D & L-FORMS/
SOL IN PYRIDINE /D-FORM/
0.3 mg/mL at 25 °C
Solubility in water, g/100ml: 0.03
Boiling Point
651 °F at 760 mmHg (NTP, 1992)
194.00 °C. @ 12.00 mm Hg
at 102.4kPa: 344 °C
194 °C (12 mm Hg)
Melting Point
279 °F (NTP, 1992)
134-138
MP:133-4 °C /D & L FORMS/
137 °C
137 °C
Vapor Pressure
1 MM HG @ 135.6 °C
Vapor pressure, Pa at 136 °C: 133
Physicochemical properties
- Melting point
- 134 · 134-138 °C(lit.)
- Boiling point
- 194 °C12 · 194 °C12 mm Hg(lit.)
- Density
- 1.31 · 1.31
- bulk density
- 350 kg/m3 · 350kg/m3
- vapor pressure
- 1.3 hPa · 1.3 hPa (136 °C)
- FEMA
- 2132 · 2132 | BENZOIN
- FLAVIS Number
- 7.028 · 07.028 | Benzoin
- Flash point
- 181 · 181
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 0.3 g/l · 0.3g/l
- form
- Powder
- pka
- 12.28 · 12.28±0.20(Predicted)
- color
- Off-white to very slightly yellow
- Odor
- agreeable vanilla-like odor
- Odor Type
- balsamic
- Water Solubility
- Soluble in chlorine. Slightly soluble in water, ethanol and ether.
- Sensitive
- Moisture Sensitive
- Merck
- 14 · 14,1093
- JECFA Number
- 836 · 836
- BRN
- 391839 · 391839
- Henry's Law Constant
- 2.2 · 2.2×105 mol/(m3Pa) at 25℃, Abraham and Jr. (2019)
- Stability
- Stable. Combustible. Incompatible with strong oxidizing agents.
- InChI
- 1S/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H
- InChIKey
- ISAOCJYIOMOJEB-UHFFFAOYSA-N
- SMILES
- OC(c1ccccc1)C(=O)c2ccccc2
- LogP
- 1.84 · 1.84-2.13 at 25℃
- Toxicology and Carcinogenesis
- Bioassay of Benzoin for Possible Carcinogenicity (CASRN 119-53-9)
- Substances Added to Food (formerly EAFUS)
- BENZOIN
- FDA 21 CFR
- 172.515 · 172.515; 73.1
- CAS DataBase Reference
- 119 · 119-53-9(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 7 J6A1NE81 · L7J6A1NE81
- NIST Chemistry Reference
- 2 · Ethanone, 2-hydroxy-1,2-diphenyl-(119-53-9)
- EPA Substance Registry System
- Benzoin (119-53-9)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P301+P312-P302+P352-P304+P340-P305+P351+P338
- Hazard Codes
- Xn
- Risk Statements
- 20 · 20/21/22-36/37/38
- Safety Statements
- 24 · 24/25-36-26
- WGK Germany
- 2 · 2
- RTECS
- 1590000 · DI1590000
- TSCA
- TSCA listed
- HS Code
- 29144090 · 29144090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazardous Substances Data
- 119 · 119-53-9(Hazardous Substances Data)
- Toxicity
- 50 orally · LD50 orally in Rabbit: 10000 mg/kg LD50 dermal Rabbit 8870 mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 68.8% (308 of 448) of all reports.
H412 (30.8%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
P273, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 448 reports by companies from 4 notifications to the ECHA C&L Inventory.
Not Classified
Hazard information
Regulatory Information
Chemical: Ethanone, 2-hydroxy-1,2-diphenyl-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Ethanone, 2-hydroxy-1,2-diphenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanone, 2-hydroxy-1,2-diphenyl- 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: 19-11-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/1899
Ethanone, 2-hydroxy-1,2-diphenyl-: Does not have an individual approval but may be used under an appropriate group standard
Fire Hazards
Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Combustible.
Fire PotentialSLIGHT, WHEN HEATED...
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes and mucous membranes. It may also cause contact dermatitis.
Hazards SummaryAn irritant; [ICSC] May cause skin and eye irritation; May be harmful if ingested, inhaled, or absorbed through the skin; Oral LD50 (rat) = 10,000 mg/kg; [MSDSonline]
FDA Requirements121.1164, LIMITATIONS: SYNTHETIC FLAVOR; 8.390, LIMITATIONS: DILUENT IN INKS FOR MARKING FRUITS & VEGETABLES. PRODUCT SPECIFICATIONS APPLY.
Reactive GroupAlcohols and Polyols
Special ReportsDHEW/NCI; Bioassay of Benzoin for Possible Carcinogenicity (1980) Technical Rpt Series No. 204 DHEW Pub No. (NIH) 80-1760
Reactivity ProfileBENZOIN is sensitive to heat and light. This chemical is incompatible with oxidizers. It reduces Fehling's solution. (NTP, 1992)
Air and Water ReactionsInsoluble in water.
Hazard Classes and Categories
Aquatic Chronic 3 (30.8%)
Not Classified
Safety & protection
Fire Fighting
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
Use water spray, powder.
First Aid Measures
Fresh air, rest.
Rinse and then wash skin with water and soap.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Spillage DisposalSweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting.
Eye PreventionWear safety spectacles.
Inhalation RiskEvaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly.
Skin PreventionProtective gloves.
Ingestion PreventionWash hands before eating.
Inhalation PreventionUse local exhaust or breathing protection.
Effects of Short Term ExposureMay cause mechanical irritation.
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Toxicology
Signs and Symptoms
Cough. Sore throat.
Redness.
Redness.
Ongoing Test Status
The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=119-53-9]
Natural Pollution SourcesNOT REPORTED FOUND IN NATURE.
Carcinogen Classification
Benzoin
TR-204: Bioassay of Benzoin for Possible Carcinogenicity (CASRN 119-53-9) (1980 )
02/15/80
No Evidence
No Evidence
No Evidence
Non-Human Toxicity Excerpts
Benzoin was found to be negative when tested for mutagenicity using the Salmonella/microsome preincubation assay, using the standard protocol approved by the National Toxicology Program (NTP). Benzoin was tested in as many as 5 Salmonella typhimurium strains (TA1535, TA1537, TA97, TA98, and TA100) in the presence and absence of rat and hamster liver S-9, at doses of 0.033, 0.0333, 0.100, 0.333, 0.3333, 0.667, 1.000, and 3.3333 mg/plate. The highest ineffective dose tested in any S. typhimurium strain was 3.3333 mg/plate. Precipitate was observed in most cultures at the high dose and also some clearing of the background bacterial lawn was also seen.
... Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Negative; Female Mice: Negative.
National Toxicology Program Studies
A bioassay of benzoin for possible carcinogenicity was conducted by incorporating the test chemical in diets of F344 rats and B6C3F1 mice. ... Groups of 50 male rats were fed diets containing 125 or 250 ppm benzoin for 104 wk, and similar groups of female rats received feed containing 250 or 500 ppm. Groups of 50 mice if each sex were fed diets containing 2,500 or 5,000 ppm benzoin for 104 wk. Groups of 50 untreated rats and mice of each sex were used as matched controls. ... Under the conditions of this bioassay, benzoin was not carcinogenic in F344 rats or B6C3F1 mice. Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Negative; Female Mice: Negative.
Regulatory information
FDA Requirements121.1164, LIMITATIONS: SYNTHETIC FLAVOR; 8.390, LIMITATIONS: DILUENT IN INKS FOR MARKING FRUITS & VEGETABLES. PRODUCT SPECIFICATIONS APPLY.
Safety data
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- DI1590000
- hs_code
- 29144090
- Toxicity
- LD50 orally in Rabbit: 10000 mg/kg LD50 dermal Rabbit 8870 mg/kg
- risk_code
- 20/21/22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 24/25-36-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P301+P312-P302+P352-P304+P340-P305+P351+P338
- Hazardous Substances Data
- 119-53-9(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Protein BindingNo pharmacokinetic data available.
Biological Half-LifeNo pharmacokinetic data available.
Metabolism/Metabolites
No pharmacokinetic data available.
BENZOIN YIELDS HYDROBENZOIN & MESO-HYDROBENZOIN IN CURVULARIA. ACKLIN, W ET AL, CROAT CHEM ACTA, 37, 11 (1965). /FROM TABLE/
Absorption, Distribution and Excretion
No pharmacokinetic data available.
No pharmacokinetic data available.
No pharmacokinetic data available.
No pharmacokinetic data available.
Cellular LocationsMembrane
Uses & manufacturing
Uses
Used as a flavor, antiseptic, photopolymerization catalyst, and in organic syntheses [HSDB]
Using Disinfectants or Biocides [Category: Clean]
IN ORGANIC SYNTHESES
PRINCIPLY AS A FLAVOR INGREDIENT; ANTISEPTIC; PHOTOPOLYMERIZATION CATALYST; INT FOR ALPHA-BENZOIN OXIME (ANALYT REAGENT FOR METALS), WETTING AGENTS, EMULSIFYING AGENTS, STILBESTROL PRODUCTS
U.S. Exports(1975) No Data
U.S. Imports(1975) No Data
U.S. Production
2023: 1,000,000 - <2,500,000 lb
(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS
(1975) PROBABLY GREATER THAN 4.5X10+5 GRAMS
Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesSurfactant (surface active agent)
Methods of Manufacturing
REACTION OF POTASSIUM CYANIDE AND BENZALDEHYDE (BENZOIN CONDENSATION)
PREPD BY TREATING AN ALCOHOLIC SOLN OF BENZALDEHYDE WITH AN ALKALI CYANIDE: ADAMS, MARVEL, ORG SYN VOL 1, PAGE 33 (1921); COLL VOL I, 88; ARNOLD, FUSON, J AM CHEM SOC 58, 1295 (1936); LF FIESER, ORGANIC EXPERIMENTS (DC HEALTH & CO, BOSTON, 1964), PAGES 211-214.
Household ProductsInformation on 2 consumer products that contain Benzoin in the following categories is provided:
Use Classification
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
Oil and Gas Drilling, Extraction, and Support activities
Ethanone, 2-hydroxy-1,2-diphenyl-: ACTIVE
REPORTED USES: NON-ALCOHOLIC BEVERAGES: 4.5 PPM; ICE CREAM, ICES, ETC: 0.54 PPM; CANDY 2.0 PPM; BAKED GOODS 1.4 PPM, GELATINS & PUDDINGS: 0.10 PPM.
SWEET FLAVORS, VANILLA, BUTTERSCOTCH. /FROM TABLE/
FEMA NUMBER: 2132
Applications
OccurrenceBenzoin is a resin from the trees of genus Styrax.
UsesBenzoin is used as a flavor, antiseptic and photopolymerization catalyst. It is also used as a raw material in organic syntheses. It serves as a precursor to benzil, which is a photoinitiator. Further, it is used as degassing agent for powder coatings. In addition to this, it is used as an additive and in powder coating to remove the pinhole phenomenon.
UsesDegassing for powder coatings
Usesbenzoin is a fragrant essential oil with bactericidal, anti-irritation, and anti-itching properties. It is considered a good ingredient for reducing skin redness and is a preservative of fats. Although its primary constituent is benzoic acid, it also contains canillin and an oily aromatic liquid. This balsamic resin is extracted by cutting deeply into the trunks of trees that grow primarily in Indonesia and Thailand.
General DescriptionOff-white to yellow-white crystalline solid with an odor of camphor. Slightly acrid taste. When broken the fresh surfaces have a milky-white color.
Upstream & downstream products
Downstream products
Suppliers1 total
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd(852)2541 2772
Additional notes
DefinitionChEBI: A ketone that consists of acetophenone bearing hydroxy and phenyl substituents at the alpha-position. The parent of the class of benzoins.
Definitionbenzoin: A colourless crystallinecompound, C6H5CHOHCOC6H5; m.p.137°C. It is a condensation product ofbenzenecarbaldehyde (benzaldehyde),made by the action of sodiumcyanide on benzenecarbaldehyde inalcoholic solution. It also occurs naturallyas the resin of a tropical tree. Itis both a secondary alcohol and a ketone,and gives reactions characteristicof both types of compound.
Related reactions
81 records
Linked notes
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