Basic information
- Standard SMILES
CCOC(=O)C(C)=O- InChIKey
XXRCUYVCPSWGCC-UHFFFAOYSA-N- Molecular formula
- C5H8O3
- Average molar mass
- 116.11 g/mol
- Monoisotopic mass
- 116.04734412
Overview
Ethyl pyruvate is an oxo carboxylic acid.
Names & identifiers
- Preferred name
- Ethyl pyruvate
- IUPAC
- ethyl 2-oxopropanoate
- English name
- Ethyl pyruvate
- Molecular formula
- C5H8O3
- Molecular weight
- 116.12
Names & synonyms
ETHYL PYRUVATEEthyl 2-oxopropanoate617-35-6Ethyl 2-oxopropionatePyruvic acid, ethyl esterPYRUVIC ACID ETHYL ESTERPropanoic acid, 2-oxo-, ethyl esterEthyl pyroracemateEthyl acetylformateFEMA No. 2457CTI-012-oxopropanoic acid ethyl ester
Show more names
Natural Ethyl pyruvatePAEEFEMA 2457ETHYL 2-OXOPROPRIONATEPropanoicacid,2-oxo-,ethylesterPYR ET
Ethyl methylglyoxylate2-oxopropionic acid ethyl esterNSC-48386DTXSID206067403O98E01OBRefChem:139052DTXCID3043104210-511-2
Database identifiers
- CAS
617-35-6- PubChem CID
- 12041
- DTXSID
DTXSID2060674- ChEMBL
CHEMBL173373- ChEBI
CHEBI:173421- UNII
- 03O98E01OB
- EC Number
- 210-511-2
- Nikkaji
- J1.665I
Properties
Computed structural properties
- XLogP
- 0.4
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 106
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Esters, Other
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesChemical shift
FragrancesFragrance Ingredient (Ethyl pyruvate) -> IFRA transparency List
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.044-1.065
Flavoring AgentsEU Flavoring substances
Solubility
slightly soluble in water; soluble in organic solvents, oils
miscible at room temperature (in ethanol)
Boiling Point
144.00 °C. @ 760.00 mm Hg
144 °C
Melting Point-50 °C
Refractive Index1.403-1.409
Physical Description
Liquid; [Merck Index] Colorless liquid with a pleasant odor; [Alfa Aesar MSDS]
Liquid
colourless liquid with a sweet, floral-fruity, warm odour
Physicochemical properties
- Melting point
- -58 °C · -58 °C
- Boiling point
- 144 °C · 144 °C (lit.)
- Density
- 1.045 g/mL · 1.045 g/mL at 25 °C (lit.)
- vapor pressure
- 2.36 hPa · 2.36hPa at 25℃
- FLAVIS Number
- 9.442 · 09.442 | Ethyl pyruvate
- refractive index
- 20 · n20/D 1.404(lit.)
- FEMA
- 2457 · 2457 | ETHYL PYRUVATE
- Flash point
- 114 °F · 114 °F
- storage temp.
- 2 °C · Store at +2°C to +8°C.
- solubility
- 10 g/l · 10g/l
- form
- Liquid
- color
- Clear pale yellow
- Odor
- 10 % · at 10.00 % in dipropylene glycol. ether fruity sweet sharp rum vegetable caramel
- Odor Type
- ethereal
- biological source
- synthetic
- Water Solubility
- Miscible with water, ethanol and ether.
- Merck
- 14 · 14,8021
- JECFA Number
- 938 · 938
- BRN
- 1071466 · 1071466
- Stability
- Volatile
- Major Application
- flavors and fragrances
- Cosmetics Ingredients Functions
- SKIN CONDITIONING
- InChI
- 1S/C5H8O3/c1-3-8-5(7)4(2)6/h3H2,1-2H3
- InChIKey
- XXRCUYVCPSWGCC-UHFFFAOYSA-N
- SMILES
- CCOC(=O)C(C)=O
- LogP
- 0.435 at · 0.435 at 22.5℃
- Substances Added to Food (formerly EAFUS)
- ETHYL PYRUVATE
- FDA 21 CFR
- 172.515 · 172.515
- CAS DataBase Reference
- 617 · 617-35-6(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 3 O98E01OB · 03O98E01OB
- NIST Chemistry Reference
- 2 · Propanoic acid, 2-oxo-, ethyl ester(617-35-6)
- EPA Substance Registry System
- 2 · Propanoic acid, 2-oxo-, ethyl ester (617-35-6)
- UNSPSC Code
- 12352108 · 12352108
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS05
- Signal word
- Danger
- Hazard statements
- 226 · H226-H314
- Precautionary statements
- 210 · P210-P233-P240-P280-P303+P361+P353-P305+P351+P338
- Hazard Codes
- Xi,F
- Risk Statements
- 10 · 10
- Safety Statements
- 16 · 16
- RIDADR
- 3272 · UN 3272 3/PG 3
- WGK Germany
- 3 · 3
- Hazard Note
- Flammable/Irritant
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- III
- HS Code
- 29183000 · 29183000
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 3 Eye · Aquatic Chronic 3Eye Dam. 1Flam. Liq. 3Skin Corr. 1B
- Toxicity
- 50 orally · LD50 orally in Rabbit: > 2000 mg/kg LD50 dermal Rat > 2000 mg/kg
- REACH Registrations
- Active
- Limited Quantities
- 5 L · 5.0 L (1.3 gallons) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
Warning
H226 (> 99.9%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1612 reports by companies from 10 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Propanoic acid, 2-oxo-, ethyl ester
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Status: Active Update: 03-10-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26714
Ethyl pyruvate: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummarySafe when used as a flavoring agent in food; [JECFA] May cause irritation; [Alfa Aesar MSDS] See Pyruvic acid.
Hazard Classes and CategoriesFlam. Liq. 3 (> 99.9%)
Safety data
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 3272 3/PG 3
- hs_code
- 29183000
- Toxicity
- LD50 orally in Rabbit: > 2000 mg/kg LD50 dermal Rat > 2000 mg/kg
- risk_code
- 10
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS05
- hazard_code
- Xi,F
- hazard_note
- Flammable/Irritant
- safety_code
- 16
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- III
- Hazard statements
- H226-H314
- Limited Quantities
- 5.0 L (1.3 gallons) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Chronic 3Eye Dam. 1Flam. Liq. 3Skin Corr. 1B
- Precautionary statements
- P210-P233-P240-P280-P303+P361+P353-P305+P351+P338
Chemistry & industry
Pharmacology
Mechanism of Action
CTI-01 inhibits the systemic release of cytokines, such as TNF-alpha and HMGB1, which promote the body's inflammatory response. The over-expression of these cytokines has been linked to diseases that occur in critical care settings, such as severe organ damage following cardiopulmonary bypass (CPB) and post-operative ileus following abdominal surgery.
Uses & manufacturing
UsesUsed as a flavoring agent; [FDA]
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationPropanoic acid, 2-oxo-, ethyl ester: ACTIVE
Applications
UsesIt can be used in the manufacture of pharmaceutical pindolol and pesticides thiabendazole. At the same time, it is an important intermediate of pharmaceutical and chemical industry. It is widely applied to various kinds of industries including medicine, pesticides, flavors and fragrances, food additives, air fresheners, fine chemicals and other industries. It can be used in the synthesis of cardiovascular drugs like expansion agent; it can also be applied to cosmetic of skin whitening and nutrition and can promote the healing of the wound, prevention and treatment of skin disease characterized by cracking, spalling and squamous metaplasia; it can be used as the high-efficiency active ingredients in the air fresheners and can effectively eliminate the ammonia and methyl mercaptan in the air; because itself has a special flavor, it can be applied to flavors, fragrance; it is also an important raw material for synthetic resins and plastics.
OccurrenceReported found in Parmesan cheese, cognac, grape wines, cocoa and mushrooms.
UsesEthyl pyruvate is used as a flavoring agent in food and anti-inflammatory agent for the treatment of critical inflammatory conditions. It is used in the treatment of critical illnesses such as severe sepsis, acute respiratory distress syndrome, burn injury, acute pancreatitis and stroke. It plays an important role in cardiac function after coronary ischemia and reperfusion.
UsesEthyl pyruvate can undergo asymmetric Henry reaction with nitromethane to form α-hydroxy β-nitro esters. It can be used as the model compound for α-ketoesters to study the mechanism of enantioselective hydrogenation reactions.
UsesEthyl pyruvate (EP) has demonstrated neuroprotective effects against acute brain injury through its anti-inflammatory action.
General DescriptionEthyl pyruvate is a volatile aliphatic ester of the pyruvate metabolite. It is present as a food additive/odor-active component in various food and beverage products. It is also used as an inhibitory odorant to repel the insects from human proximity.
Preparation methods
PreparationBy direct esterification of pyruvic acid with absolute ethyl alcohol at the boil and subsequent vacuum distillation; by esterification via oxidation of vapors of ethyl lactate in the presence of V2O5 at 155°C
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通小竹生物医药有限公司18015606981 · [email protected]
北京安司莫森技术有限公司010-82954736 13391601435 · [email protected]
韶远科技（上海）有限公司021-50795510 4000665055 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]
Syntechem Co.,Ltd[email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
阿法埃莎（中国）化学有限公司400-6106006 · [email protected]
安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [email protected]
武汉凯威斯科技有限公司86-027-67849912 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
吉良化学21-62165282 · [email protected]
上海景颜化工科技有限公司13817811078 · [email protected]
嘉兴市艾森化工有限公司0573-85285100 18627885956 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
上海长根化学科技有限公司021-69106814 13917161715
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
玛雅试剂+86 (573) 82222445 (0)18006601000 452520369 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
河南蔚源生物科技有限公司0371-27990887 13703782753 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
上海京福生物科技有限公司0598-5859955 13313739955 · [email protected]
南京维奥化工有限公司Please Send Email 18652950785 · [email protected]
河南多贝化工有限公司0370-2785118 17550508557 · [email protected]
斯百全化学（上海）有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
北京泰亚杰科技有限公司021-33690831-8001 13552411790;18616022633 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
赛默飞世尔科技（中国）有限公司800-810-5118 · [email protected]
江苏艾康生物医药研发有限公司025-66113011 13913916777 · [email protected]
上海健超生物科技有限公司150-2103-5486 18017383231 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
上海贤鼎生物科技有限公司4009209199 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
深圳康特腾科技有限公司86-0755-86635001 · [email protected]
越林试剂021-62960152 · [email protected]
无锡中坤生化科技有限公司+86 0510-85629785
上海汇凯化学科技有限公司021-61995394 18916691159 · [email protected]
湖北朗昕生化药业有限公司86-714-6395877
湖北省圣宝莱生物科技有限公司027-59105235 13007105135 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
Additional notes
DefinitionChEBI: Ethyl pyruvate is an oxo carboxylic acid.
Related reactions
327 records
Linked notes
Loading…