Ethyl 3-phenylglycidate

HCID 8469CAS 121-39-1

Basic information

Standard SMILES
CCOC(=O)C1OC1c1ccccc1
InChIKey
GOMAKLPNAAZVCJ-UHFFFAOYSA-N
Molecular formula
C11H12O3
Average molar mass
192.21 g/mol
Monoisotopic mass
192.07864424

Names & identifiers

Preferred name
Ethyl 3-phenylglycidate
IUPAC
ethyl 3-phenyloxirane-2-carboxylate
English name
Ethyl 3-phenylglycidate
Molecular formula
C11H12O3
Molecular weight
192.21

Names & synonyms

Ethyl 3-phenylglycidate121-39-1Ethyl 3-phenyloxirane-2-carboxylateEthyl phenylglycidateETHYL 2,3-EPOXY-3-PHENYLPROPIONATEOxiranecarboxylic acid, 3-phenyl-, ethyl esterGlycidic acid, 3-phenyl-, ethyl esterFEMA No. 2454DTXSID80258863-Phenylglycidic acid, ethyl esterEthyl 3-phenyl-2,3-epoxypropionateEthyl alpha,beta-epoxyhydrocinnamate
Show more names
FEMA 2454ethyl3-phenyloxiraneβ-epoxyhydrocinnamatestrawberry glycidate 2ethyl3-phenyloxirane-2-ETHYL PHENYLGLYCIDATE FCCEthyl 3-Phenylglycidate ETHYL A B-EPOXYHYDROCINNAMATE
2VVS520ZWMEthyl alpha,beta-epoxy-alpha-phenylpropionateNSC-8899DTXCID9058862-Oxiranecarboxylic acid, 3-phenyl-, ethyl ester3-EPGethyl-3-phenylglycidateRefChem:138719

Database identifiers

CAS
121-39-1、54276-44-7
PubChem CID
8469
DTXSID
DTXSID8025886
ChEMBL
CHEMBL1369819
ChEBI
CHEBI:173922
UNII
2VVS520ZWM
EC Number
204-467-3
Nikkaji
J122.448D

Properties

Computed structural properties

XLogP
1.7
Topological polar surface area
38.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
4
Heavy atoms
14

Experimental & physicochemical properties

pHACID VALUE: NOT MORE THAN 1.0
OdorSTRONG FRUITY ODOR SUGGESTIVE OF STRAWBERRY
TasteSWEET TASTE CORRESPONDING TO FRUITY ODOR
Density · 3 items

1.122 (NTP, 1992) - Denser than water; will sink

1.120-1.128 @ 25/25 °C

1.120-1.125

Color/FormCOLORLESS TO PALE-YELLOW LIQUID
Solubility · 4 items

Slightly soluble (1-10 mg/ml) (NTP, 1992)

1:6 IN 70% ALCOHOL; 1:1 IN 80% ALCOHOL

Insoluble in water; Soluble in ether, oils

Soluble (in ethanol)

Physicochemical properties

Melting point
17 · 17-18 °C
Boiling point
96 °C/0.5 · 96 °C/0.5 mmHg (lit.)
Density
1.102 g/mL · 1.102 g/mL at 25 °C (lit.)
vapor pressure
0.12 Pa · 0.12Pa at 24℃
FEMA
2454 · 2454 | ETHYL 3-PHENYLGLYCIDATE
refractive index
20 · n20/D 1.518(lit.)

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H317 (99.6%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1593 reports by companies from 6 notifications to the ECHA C&L Inventory.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 4 items

Chemical: Oxiranecarboxylic acid, 3-phenyl-, ethyl ester

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

Status: Active Update: 25-01-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/22103

Oxiranecarboxylic acid, 3-phenyl-, ethyl ester: Does not have an individual approval but may be used under an appropriate group standard

Fire HazardsThis chemical is probably combustible. (NTP, 1992)
Hazards SummaryA mutagen; [RTECS] No sensitization reactions in 25 human volunteers; [HSDB] May polymerize in contact with catalysts or heat; [CAMEO] Safe when used as a flavoring agent in food; [JECFA] An irritant; [MSDSonline]
FDA RequirementsFDA 121.1164
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters;Epoxides;Polymerizable Compounds
Reactivity AlertsPolymerizable

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
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.;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)

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong 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 store this material in a refrigerator. (NTP, 1992)

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

Human Toxicity Excerpts · 1 item

TESTED AT 4% IN PETROLATUM, IT PRODUCED NO IRRITATION AFTER A 48-HOUR CLOSED-PATCH TEST IN 25 HUMAN SUBJECTS. A MAXIMIZATION TEST WAS CARRIED OUT ON 25 VOLUNTEERS. THE MATERIAL WAS TESTED AT A CONCENTRATION OF 4% IN PETROLATUM AND PRODUCED NO SENSITIZATION REACTIONS.

Non-Human Toxicity ExcerptsETHYL PHENYLGLYCIDATE APPLIED FULL STRENGTH TO INTACT OR ABRADED RABBIT SKIN UNDER OCCLUSION WAS NOT IRRITATING.

Regulatory information

Regulatory Information · 4 items

Chemical: Oxiranecarboxylic acid, 3-phenyl-, ethyl ester

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

Status: Active Update: 25-01-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/22103

Oxiranecarboxylic acid, 3-phenyl-, ethyl ester: Does not have an individual approval but may be used under an appropriate group standard

FDA RequirementsFDA 121.1164

Safety data

PPE
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
wgk
2
tsca
TSCA listed
rtecs
MB4970000
hs_code
29189990
Toxicity
The acute oral LD50 value in rats was reported as 2.3 ml/kg (2.0-2.6 ml/ kg) (Shelanski, 1973b). The acute dermal LD50 value in rabbits was reported as > 5 g/kg (Shelanski, 1973a).

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm;Extracellular

Uses & manufacturing

Uses · 5 items

Used as a flavor ingredient and a fragrance in soaps, detergents, creams, lotions, and perfumes; [HSDB]

AS FRAGRANCE IN SOAPS, DETERGENTS, CREAMS, LOTIONS, PERFUME

IN BERRY & CHERRY FOOD FLAVORINGS

FLAVORING AGENT IN GELATINS, PUDDINGS & BAKED GOODS

FLAVORING AGENT IN CANDY, ICE CREAM & BEVERAGES

U.S. Exports · 2 items

(1979) No Data

(1981) No Data

U.S. Imports · 2 items

(1980) 6.01X10+5 GRAMS (PRINCPL CUSTMS DISTS)

(1981) 1.82X10+3 GRAMS (PRINCPL CUSTMS DISTS)

U.S. Production · 2 items

(1979) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1981) PROBABLY GREATER THAN 4.54X10+5 GRAMS

Methods of Manufacturing · 2 items

BY THE REACTION OF BENZALDEHYDE AND THE ETHYL ESTER OF MONOCHLORACETIC ACID IN THE PRESENCE OF AN ALKALINE CONDENSING AGENT: BEDOUKIAN PZ, PERFUMERY AND FLAVORING SYNTHETICS 2ND EDITION, 297 (1967), ELSEVIER PUBLISHING COMPANY, NEW YORK.

REACTION OF BENZALDEHYDE WITH ETHYL MONOCHLORACETATE IN PRESENCE OF AN ALKALINE CONDENSING AGENT; REACTION OF THE SILVER SALT OF PHENYL GLYCIDIC ACID WITH ETHYL IODIDE

Household ProductsInformation on 3 consumer products that contain Ethyl 3-Phenylglycidate in the following categories is provided:;• Personal Care
Applications · 3 items

OccurrenceApparently has not been reported to occur in nature.

UsesEthyl 3-Phenyloxirane-2-carboxylate is used in preparation method of early-strength viscosity-breaking Polycarboxylate water reducer containing three viscosity-breaking group and used as concrete additive.

General DescriptionClear pale yellow or yellow liquid.

Preparation methods

PreparationUsually prepared by the reaction of benzaldehyde and the ethyl ester of monochloracetic acid in the presence of an alkaline condensing agent; by reacting the silver salt of phenyl glycidic acid with ethyl iodide.

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
Hebei Zhuanglai Chemical Trading Co Ltd+86-16264648883 · [email protected]
山东泰诚生物科技有限公司18769832557 18769832557 · [email protected]
毕佳索(上海毕得医药科技股份有限公司)400-6005915 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]

Additional notes

DefinitionChEBI: Ethyl phenylglycidate is an epoxide and a carboxylic acid.

Related reactions

8 records

Linked notes

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