Ethyl 3-phenylglycidate
Basic information
- CAS
121-39-1- Standard SMILES
CCOC(=O)C1OC1c1ccccc1- InChIKey
GOMAKLPNAAZVCJ-UHFFFAOYSA-N- Molecular formula
- C11H12O3
- Average molar mass
- 192.21 g/mol
- Monoisotopic mass
- 192.07864424
Overview
Ethyl-3-phenylglycidate appears as clear pale yellow or yellow liquid. (NTP, 1992)
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
- Formal charge
- 0
- Complexity
- 209
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Other Aromatic Compounds
pHACID VALUE: NOT MORE THAN 1.0
FragrancesFragrance Ingredient (Ethyl 3-phenylglycidate) -> IFRA transparency List
OdorSTRONG FRUITY ODOR SUGGESTIVE OF STRAWBERRY
TasteSWEET TASTE CORRESPONDING TO FRUITY ODOR
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density
1.122 (NTP, 1992) - Denser than water; will sink
1.120-1.128 @ 25/25 °C
1.120-1.125
Flavoring AgentsEU Flavoring substances
Color/FormCOLORLESS TO PALE-YELLOW LIQUID
Solubility
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)
Flash Point
greater than 200 °F (NTP, 1992)
100 °C
Boiling Point
509 to 518 °F at 760 mmHg (NTP, 1992)
96 °C (0.5 mm Hg)
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.)
- FLAVIS Number
- 16.018 · 16.018 | Ethyl 3-phenyl-2,3-epoxypropionate
- Flash point
- 230 °F · >230 °F
- storage temp.
- 2 · 2-8°C
- solubility
- Insoluble in water
- form
- Liquid
- color
- Clear colorless to yellow
- Odor
- 100 % · at 100.00 %. sweet strawberry berry floral tropical
- Odor Type
- fruity
- biological source
- synthetic
- Water Solubility
- 748.4 mg/L · 748.4mg/L at 24℃
- Sensitive
- Moisture Sensitive
- JECFA Number
- 1576 · 1576
- Stability
- Stable. Combustible. Incompatible with strong oxidizing agents.
- Major Application
- flavors and fragrances
- Cosmetics Ingredients Functions
- PERFUMING
- InChI
- 1S/C11H12O3/c1-2-13-11(12)10-9(14-10)8-6-4-3-5-7-8/h3-7,9-10H,2H2,1H3
- InChIKey
- GOMAKLPNAAZVCJ-UHFFFAOYSA-N
- SMILES
- CCOC(=O)C1OC1c2ccccc2
- LogP
- 2.4 at · 2.4 at 20℃
- CAS DataBase Reference
- 121 · 121-39-1(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- 3 · ETHYL 3-PHENYLGLYCIDATE
- FDA 21 CFR
- 172.515 · 172.515
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 2 VVS520ZWM · 2VVS520ZWM
- EPA Substance Registry System
- 3 · Ethyl 3-phenylglycidate (121-39-1)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 303 · H303-H335-H315-H319
- Precautionary statements
- 264 · P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a
- PPE
- Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 23 · 23-24/25
- WGK Germany
- 2 · 2
- RTECS
- 4970000 · MB4970000
- TSCA
- TSCA listed
- HS Code
- 29189990 · 29189990
- Storage Class
- 10 · 10 - Combustible liquids
- Hazardous Substances Data
- 121 · 121-39-1(Hazardous Substances Data)
- Toxicity
- 50 value · 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).
- REACH Registrations
- Active
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
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.
Hazard information
Regulatory Information
Chemical: Oxiranecarboxylic acid, 3-phenyl-, ethyl ester
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
REACH registered substance: Ethyl 3-phenyloxirane-2-carboxylate (EC: 204-467-3)
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
Reactivity AlertsPolymerizable
Reactivity Profile
Epoxides are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts.
Air and Water ReactionsSlightly water soluble.
Hazard Classes and CategoriesSkin Sens. 1B (99.6%)
Safety & protection
Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
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 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.
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
Human Toxicity Excerpts
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
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).
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 23-24/25
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H303-H335-H315-H319
- REACH Registrations
- Active
- Precautionary statements
- P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a
- Hazardous Substances Data
- 121-39-1(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
Uses
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
(1979) No Data
(1981) No Data
U.S. Imports
(1980) 6.01X10+5 GRAMS (PRINCPL CUSTMS DISTS)
(1981) 1.82X10+3 GRAMS (PRINCPL CUSTMS DISTS)
U.S. Production
(1979) PROBABLY GREATER THAN 4.54X10+5 GRAMS
(1981) PROBABLY GREATER THAN 4.54X10+5 GRAMS
Methods of Manufacturing
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:
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
General Manufacturing Information
2-Oxiranecarboxylic acid, 3-phenyl-, ethyl ester: ACTIVE
ASSAY: 99% MIN (98%).
CONCENTRATION IN FINAL PRODUCT (%): SOAP: USUAL 0.01, MAXIMUM 0.1; DETERGENT: USUAL 0.001, MAXIMUM 0.01; CREAMS, LOTIONS: USUAL 0.01, MAXIMUM 0.05; PERFUME: USUAL 0.15, MAXIMUM 0.4.
REPORTED USES: NON-ALCOHOLIC BEVERAGES 4.6 PPM, ICE CREAMS, ICES, ETC 12 PPM, CANDY 18 PPM, BAKED GOODS 20 PPM, GELATINS AND PUDDINGS 10-70 PPM.
THE COUNCIL OF EUROPE (1970) INCLUDED ETHYL PHENYLGLYCIDATE IN ITS LIST OF TEMPORARILY ADMISSIBLE ARTIFICIAL FLAVORING SUBSTANCES.
FEMA 2454
Applications
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.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: Ethyl phenylglycidate is an epoxide and a carboxylic acid.
Related reactions
8 records
Compound notes
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