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Benzoin

HCID 8400
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
119-53-9
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-Phenylbenzoyl carbinol(+-)-Benzoinalpha-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 propertiesFilling in

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
LogP · 2 items

2.130

2.13

OdorSWEET NON-DESCRIPT ODOR
TasteSWEET NON-DESCRIPT TASTE
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 2 items

1.31 at 68 °F (NTP, 1992) - Denser than water; will sink

1.31 g/cm³

Flavoring AgentsEU Flavoring substances
Color/Form · 2 items

PALE YELLOW CRYSTALS

WHITE CRYSTALS

Solubility · 6 items

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/

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

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 · 5 items

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)

REACH registered substance: Benzoin (EC: 204-331-3)

Ethanone, 2-hydroxy-1,2-diphenyl-: Does not have an individual approval but may be used under an appropriate group standard

Fire Hazards · 2 items

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]

Chemistry & industry

Pharmacology

Protein BindingNo pharmacokinetic data available.
Biological Half-LifeNo pharmacokinetic data available.
Metabolism/Metabolites · 2 items

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 · 4 items

No pharmacokinetic data available.

No pharmacokinetic data available.

No pharmacokinetic data available.

No pharmacokinetic data available.

Cellular LocationsMembrane

Uses & manufacturing

Uses · 4 items

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 · 3 items

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 Uses

Related reactions

81 records
New reaction record
HRID 67234 reaction equation
HRID 67234As reactantuspto-grants-1982_08
HRID 67238 reaction equation
HRID 67238As reactantuspto-grants-1982_08
HRID 67239 reaction equation
HRID 67239As reactantuspto-grants-1982_08
HRID 86388 reaction equation
HRID 86388As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 117849 reaction equation
HRID 117849As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 206669 reaction equation
HRID 206669As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 227343 reaction equation
HRID 227343As reactantuspto-grants-2009_07
HRID 257618 reaction equation
HRID 257618As reactantuspto-grants-1993_11
Page 1 of 11

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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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 · 4 items

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 · 5 items

279 °F (NTP, 1992)

134-138

MP:133-4 °C /D & L FORMS/

137 °C

137 °C

Vapor Pressure · 2 items

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
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 · 2 items

Aquatic Chronic 3 (30.8%)

Not Classified

Safety & protection

Fire Fighting · 2 items

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 · 3 items

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 · 1 item

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 · 1 item

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) · 1 item

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 · 3 items

Cough. Sore throat.

Redness.

Redness.

Ongoing Test Status · 1 item

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 · 6 items

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 · 2 items

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 · 1 item

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)
Surfactant (surface active agent)
Methods of Manufacturing · 2 items

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 · 2 items

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 5 items

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 · 5 items

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

4,5-DIPHENYL-2-IMIDAZOLETHIOLBenzil2-(2-Chlorophenyl)-4,5-diphenylimidazole2,3-DIPHENYLQUINOXALINEBENZOIN ISOPROPYL ETHER"6,7-diphenyl-2-sulfanylidene-1H-pteridin-4-oneTetraphenylcyclopentadienone2,4,5-TriphenylimidazolePyridine, 4-(4,5-diphenyl-1H-imidazol-2-yl)-
Additional notes · 2 items

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.