Ethyl acrylate
Relevant Data
Food Additives Approved in the United States:
Food Additives Approved by WHO:
General Information
| Chemical name | Ethyl acrylate |
| CAS number | 140-88-5 |
| COE number | 245 |
| JECFA number | 1351 |
| Flavouring type | substances |
| FL No. | 09.037 |
| Mixture | No |
| Purity of the named substance at least 95% unless otherwise specified |
From webgate.ec.europa.eu
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 8821 |
| IUPAC Name | ethyl prop-2-enoate |
| InChI | InChI=1S/C5H8O2/c1-3-5(6)7-4-2/h3H,1,4H2,2H3 |
| InChI Key | JIGUQPWFLRLWPJ-UHFFFAOYSA-N |
| Canonical SMILES | CCOC(=O)C=C |
| Molecular Formula | CH2CHCOOC2H5 |
| Wikipedia | ethyl acrylate |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 100.117 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 3 |
| Complexity | 76.1 |
| CACTVS Substructure Key Fingerprint | A A A D c c B g M A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A G g A A A A A A C A C g g A I C C A A A B A C I A C D S C A A A A A A A A A A I A A A A A E A A B A A A I A A C A A A A A A A A I I A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 26.3 |
| Monoisotopic Mass | 100.052 |
| Exact Mass | 100.052 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 7 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9709 |
| Human Intestinal Absorption | HIA+ | 0.9954 |
| Caco-2 Permeability | Caco2+ | 0.7013 |
| P-glycoprotein Substrate | Non-substrate | 0.7919 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8876 |
| Non-inhibitor | 0.9147 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9080 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5626 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8369 |
| CYP450 2D6 Substrate | Non-substrate | 0.9289 |
| CYP450 3A4 Substrate | Non-substrate | 0.7407 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6474 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9069 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9568 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8965 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9457 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8098 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9619 |
| Non-inhibitor | 0.9802 | |
| AMES Toxicity | Non AMES toxic | 0.9132 |
| Carcinogens | Carcinogens | 0.7185 |
| Fish Toxicity | High FHMT | 0.9210 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.7918 |
| Honey Bee Toxicity | High HBT | 0.8518 |
| Biodegradation | Ready biodegradable | 0.8818 |
| Acute Oral Toxicity | III | 0.7588 |
| Carcinogenicity (Three-class) | Non-required | 0.5124 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.6773 | LogS |
| Caco-2 Permeability | 1.3302 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0656 | LD50, mol/kg |
| Fish Toxicity | 0.8007 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.1936 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | Inhalation ; oral ; dermal ; eye contact . |
|---|---|
| Mechanism of Toxicity | Ethyl acrylate causes gastric lesions depending upon upon the rate of chemical delivery to stomach tissue as a result of interaction of the parent molecule or metabolites (other than hydrolysis products), with subcellular sites in stomach tissue . |
| Metabolism | Ethyl acrylate is hydrolized to acrylic acid in liver, kidney, and lung homogenates. It is suggested to bind to glutathione spontaneaoulsy and after catalysis by liver glutathione-S-transferase. The major metabolites of ethyl acrylate are mercapturic acids od ethyl acrylate and acrylic acid. Three metabolites were identified in a study: 3-hydroxypropionic acid and two mercapturic acids. N-Acetyl-S-(2-carboxyethyl)cysteine arises by glutathione conjugation of acrylic acid, while N-acetyl-S-(2-carboxyethyl)cysteine ethyl ester derives from the conjugation of intact ethyl acrylate.(A347, A635, A664, ). |
| Toxicity Values | LD50: 760-1020 mg/kg (Oral, Rat) LC50: 1000-2000 ppm over 4 hours (Inhalation, Rat) |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | 2B, possibly carcinogenic to humans. |
| Minimum Risk Level | None |
| Health Effects | Thickened forestomach mucosa, forestomach inflammation and lesions, and abdominal adhesions; swelling of renal tubules and the liver, minor lesions on the liver and lung, and increased kidney weight may result from poisoning (L1242). |
| Treatment | For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport. Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal. |
| Reference |
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From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Acrylic acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Acrylic acid esters |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Acrylic acid ester - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Carboxylic acid ester - Monocarboxylic acid or derivatives - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as acrylic acid esters. These are organic compounds containing and ester acrylic acid (CH2=CHC(=O)OH). |
From ClassyFire