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Home > Encyclopedia > (±)-Benzoin

(±)-Benzoin

pharmaceutical raw materials
(±)-Benzoin structure

(±)-Benzoin 

structure
  • CAS No:

    119-53-9

  • Formula:

    C14H12O2

  • Chemical Name:

    (±)-Benzoin

  • Synonyms:

    Ethanone,2-hydroxy-1,2-diphenyl-;Benzoin;2-Hydroxy-1,2-diphenylethanone;Benzoylphenylcarbinol;α-Hydroxy-α-phenylacetophenone;2-Hydroxy-2-phenylacetophenone;α-Hydroxybenzyl phenyl ketone;2-Hydroxy-1,2-diphenyl-1-ethanone;Wy 42956;Desyl alcohol;1,2-Diphenyl-1-hydroxy-2-ethanone;dl-Benzoin;(±)-Benzoin;DL-Benzoin;(±)-2-Hydroxy-1,2-diphenylethanone;(±)-2-Hydroxy-2-phenylacetophenone;(RS)-Benzoin;Nisso Cure MB;NSC 8082;1,2-Diphenyl-2-hydroxyethanone;1,2-Diphenyl-2-oxoethanol;α-Benzoylbenzenemethanol;S 19;S 19 (benzoin);Esacure EB 3;2-Hydroxy-1-phenyl-2-phenylethanone;Seikuol Z;2-Hydroxyl-1,2-phenylethanone;2-Phenyl-2-hydroxyacetophenone;F 297;Jiqi GK 19;GK 19;L 307;LC Benzoin;AW 63;AHA 4100;ZR-A 401;KV 203;579-44-2

  • Categories:

    Specialty Chemicals

Description

WHITE-TO-YELLOW CRYSTALS.


Benzoin is an organic compound with the formula PhCH(OH)C(O)Ph. It is a hydroxy ketone attached to two phenyl groups. It appears as off-white crystals, with a light camphor-like odor. Benzoin is synthesized from benzaldehyde in the benzoin condensation. It is chiral and it exists as a pair of enantiomers: (R)-benzoin and (S)-benzoin.


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)|DryPowder|Solid|WHITE-TO-YELLOW CRYSTALS.|white to light yellow crystals with a faint, sweet, balsamic odour


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)|Benzoin is a ketone that consists of acetophenone bearing hydroxy and phenyl substituents at the alpha-position. The parent of the class of benzoins. It has a role as an EC 3.1.1.1 (carboxylesterase) inhibitor. It is a member of benzoins and a secondary alpha-hydroxy ketone.|Benzoin is a white crystalline compound prepared by condensation of benzaldehyde in potassium cyanide, and is used in organic syntheses. This should not be confused with benzoin gum from STYRAX (see [DB11222]). Benzoin is an FDA-approved colour additive used for marking fruits and vegetables.|A white crystalline compound prepared by condensation of benzaldehyde in potassium cyanide and used in organic syntheses. This should not be confused with benzoin gum from STYRAX.

(±)-Benzoin Basic Attributes

212.24

212.24

391839

204-331-3

1214

8082

DTXSID1020144

PALE YELLOW CRYSTALS|WHITE CRYSTALS|REDDISH-BROWN GLOBULES

2914400090

Characteristics

37.3

2.1

Off-white to very slightly yellow Powder

1.310 g/cm3

137 °C

344 °C @ Press: 760.0 Torr

181

1.609

soluble in chlorine. Slightly soluble in water, ethanol and ether.

2-8°C

1 MM HG @ 135.6 DEG C

Oral-rat LD50: 10000 mg/kg; Skin-rabbit LD50; 8870 mg/kg

Flammable; burning produces irritating smoke

SWEET NON-DESCRIPT ODOR

SWEET NON-DESCRIPT TASTE

ALC SOLN IS ACID TO LITMUS PAPER & BECOMES MILKY UPON ADDITION OF WATER

REDUCES FEHLING'S SOLN /DL-FORM/|NEEDLES FROM METHANOL /L-FORM/; NEEDLES /D-FORM/|SIX-SIDED MONOCLINIC PRISMS FROM ALCOHOL /DL-FORM/|BP:344 °C @ 768 MM HG; MP:137 °C; DENSITY: 1.310 @ 20 °C/4 °C /DL-FORM/|SPECIFIC OPTICAL ROTATION: -117.5 DEG @ 12 °C/D (ACETONE, 1.25%) /L-FORM/|SPECIFIC OPTICAL ROTATION: +92.8 DEG @ 15 °C/D (PYRIDINE, 1%) /D-FORM/|MAX ABSORPTION (ALCOHOL): 248 NM (LOG E= 4.1); SADTLER REFERENCE NUMBER: 2722 (IR, PRISM); 736 (UV); SOL IN HOT ACETIC ACID; CHLOROFORM /DL-FORM/|SWEET, BALSAMIC, PLEASANT ODOR; AROMATIC, ACRID, BITTERSWEET TASTE /SIAM OR SUMATRA BENZOIN/|RESIN BECOMES PLASTIC WHEN CHEWED|BRITTLE @ ROOM TEMP, BUT SOFTENED BY HEAT

Insoluble in water.

Alcohols and Polyols

BENZOIN is sensitive to heat and light. This chemical is incompatible with oxidizers. It reduces Fehling's solution. (NTP, 1992)

Safety Information

NONH for all modes of transport

2

20/21/22-36/37/38

24/25-36-26

DI1590000

Xn

Warehouse ventilated, low temperature and dry

Stable. Combustible. Incompatible with strong oxidizing agents.

P273, P501

H412

121.1164, LIMITATIONS: SYNTHETIC FLAVOR; 8.390, LIMITATIONS: DILUENT IN INKS FOR MARKING FRUITS & VEGETABLES. PRODUCT SPECIFICATIONS APPLY.|FDA NUMBER: 121.1163; LIMITATIONS: NATURAL FLAVOR.

DHEW/NCI; Bioassay of Benzoin for Possible Carcinogenicity (1980) Technical Rpt Series No. 204 DHEW Pub No. (NIH) 80-1760

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)|Combustible.

H412 (98.56%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]|P273, and P501|Aggregated GHS information provided by 446 companies from 4 notifications to the ECHA C&L Inventory.| |Warning|H315 (99.85%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, and P501|Aggregated GHS information provided by 1386 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P260, P261, P264, P270, P272, P280, P302+P352, P305+P351+P338, P310, P314, P321, P333+P313, P363, and P501|Aggregated GHS information provided by 7 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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.

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. STORAGE PRECAUTIONS: You should protect this material from exposure to light. Keep it away from oxidizing materials and store it under refrigerated temperatures. (NTP, 1992)

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)

SLIGHT, WHEN HEATED...

Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting.

Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly.

May cause mechanical irritation.

Use local exhaust or breathing protection.

Protective gloves.

Wear safety spectacles.

Toxicity

practically nontoxic

Oral LD50 in rat is 10,000 mg/kg and dermal LD50 in rabbit is 8870 mg/kg [MSDS].

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.

No pharmacokinetic data available.

NOT REPORTED FOUND IN NATURE.|BALSAMIC RESIN FROM STYRAX BENZOIN DRYAND, KNOWN AS SUMATRA BENZOIN, OR FROM STYRAX TONKINENSIS (PIERRE) CRAIB, STYRACACEAE OR OTHER SPECIES OF STYRAX KNOWN AS SIAM BENZOIN. HABITAT: THAILAND, CAMBODIA, SOUTH VIETNAM, SUMATRA, JAVA, & SUNDA ISLANDS.

Drug Information

No approved therapeutic indications.

3. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5.0 G/KG, BETWEEN 1 OUNCE & 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB).

No pharmacokinetic data available.

No pharmacokinetic data available.|BENZOIN YIELDS HYDROBENZOIN & MESO-HYDROBENZOIN IN CURVULARIA. ACKLIN, W ET AL, CROAT CHEM ACTA, 37, 11 (1965). /FROM TABLE/

No pharmacokinetic data available.

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes and mucous membranes. It may also cause contact dermatitis. ACUTE/CHRONIC HAZARDS: This compound may be harmful by ingestion, inhalation or skin absorption. It may cause irritation of the skin, eyes and mucous membranes. When heated to decomposition it emits acrid smoke, irritating fumes and toxic fumes of carbon monoxide and carbon dioxide. (NTP, 1992)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)


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.

2 hydroxy 1,2 diphenylethanone

Cough. Sore throat.


Redness.


Redness.

(±)-Benzoin Use and Manufacturing

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.|EXTRACTION OF NATURAL BENZOIN OBTAINED FROM VARIOUS SPECIES OF THE TREE, STYRAX, WITH BENZENE, FOLLOWED BY DISTILLATION OF THE SOLVENT

Uses

Degassing for powder coatings


Paint additives and coating additives not described by other categories


Paints and coatings

Production

100,000 - 500,000 lb|(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1975) PROBABLY GREATER THAN 4.5X10+5 GRAMS|(1972) NONE

GRADES: TECHNICAL; TINCTURE USP.

Paint and coating manufacturing|Ethanone, 2-hydroxy-1,2-diphenyl-: ACTIVE|Gum benzoin: 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|CONSTITUENTS: ETHEREAL OIL, FREE & COMBINED BENZOIC & CINNAMIC ACIDS UP TO 39%, VANILLIN, CONIFERYL BENZOATE, RESIN (A MIXTURE OF BENZORESINOL & BENZORESINOTANNOL) ESTERIFIED WITH BENZOIC ACID, STYROL, STYRACIN. /SIAM BENZOIN & SUMATRA BENZOIN/|NOT LESS THAN 90% OF SIAM & NOT LESS THAN 75% OF SUMATRA BENZOIN IS SOL IN ALCOHOL (USP). /SIAM & SUMATRA BENZOIN/|THE CHEMICAL DIFFERENCES BETWEEN SIAM & SUMATRA VARIETIES DERIVE FROM THE LEVELS OF CINNAMIC & BENZOIC ACIDS & THEIR CORRESPONDING ESTERS; BENZOIC DERIVATIVES PREVAIL IN SIAM BENZOIN, WHILE CINNAMIC DERIVATIVES PREVAIL IN SUMATRA BENZOIN. /SIAM BENZOIN & SUMATRA BENZOIN/|/FROM/ TREES OF.../STYRAX BENZOIN, PARALLELONEURUS, & TONKINENSIS/...RESIN FLOWS FROM INCISIONS MADE IN THE BARK.|For more General Manufacturing Information (Complete) data for GUM BENZOIN (14 total), please visit the HSDB record page.

Food additives -> Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes|Flavoring Agents -> JECFA Flavorings Index|Cosmetics -> Film forming

Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT;

Computed Properties

Molecular Weight:212.24
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:212.083729621
Monoisotopic Mass:212.083729621
Topological Polar Surface Area:37.3
Heavy Atom Count:16
Complexity:225
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Dahuo Luo Pills have the effects of dilating blood vessels, resisting myocardial ischemia, and inhibiting thrombosis. While increasing cerebral blood flow, it does not significantly increase myocardial oxygen consumption. It is of great significance for hemiplegia caused by stroke, improving atherosclerosis, and anti-inflammation and analgesia.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

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