Basic information
- CAS
3724-65-0- Standard SMILES
C/C=C\C(=O)O- InChIKey
LDHQCZJRKDOVOX-IHWYPQMZSA-N- Molecular formula
- C4H6O2
- Average molar mass
- 86.09 g/mol
- Monoisotopic mass
- 86.03677943
Overview
Isocrotonic acid is a but-2-enoic acid having a cis- double bond at C-2. It is a conjugate acid of an isocrotonate.
Names & identifiers
- Preferred name
- Isocrotonic acid
- IUPAC
- (Z)-but-2-enoic acid
- English name
- Crotonic acid
- Molecular formula
- C4H6O2
- Molecular weight
- 86.09
Names & synonyms
Isocrotonic acidcis-Crotonic Acidcis-2-Butenoic Acid(Z)-Crotonic acid(Z)-but-2-enoic acid(Z)-2-Butenoic acid(2Z)-2-Butenoic acid2Z-butenoic acidCrotonic acid, (Z)-b-Crotonic acidUNII-85GQ7GL1UMperisocrotonic acid
Show more names
2-BUTENOIC ACIDBUT-2-ENOIC ACIDcrotonicFEMA 3908BUTENOIC ACID(2E)-but-2-enoic acidCH3CH=CHCOOHa-butenoicacid1-PROPENE-1-CARBOXYLIC ACIDC01771
85GQ7GL1UMEINECS 207-973-2(Z)-CH3CH=CHCOOHISOCROTONIC ACID [MI]CHEBI:36253DTXSID70880977C4:1n-2Perisocrotonate
Database identifiers
- CAS
3724-65-0、503-64-0- PubChem CID
- 643792
- DTXSID
DTXSID70880977- ChEBI
CHEBI:36253- UNII
- 85GQ7GL1UM
- EC Number
- 207-973-2
- Nikkaji
- J2.604B
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 6
- Formal charge
- 0
- Complexity
- 73.6
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]
SpringerMaterials PropertiesBoiling point
Solubility1000 mg/mL at 20 °C
Boiling Point169.00 °C. @ 760.00 mm Hg
Melting Point14.6 °C
Physical DescriptionLiquid
Physicochemical properties
- Melting point
- 70 · 70-72 °C(lit.)
- Boiling point
- 180 · 180-181 °C(lit.)
- Density
- 1.027 g/mL · 1.027 g/mL at 25 °C(lit.)
- vapor density
- 2.97 · 2.97 (vs air)
- vapor pressure
- 0.19 mm · 0.19 mm Hg ( 20 °C)
- refractive index
- 1.421 · 1.4210 (estimate)
- FEMA
- 3908 · 3908 | (E)-2-BUTENOIC ACID
- FLAVIS Number
- 8.072 · 08.072 | But-2-enoic acid (cis and trans)
- Flash point
- 190 °F · 190 °F
- storage temp.
- 2 · 2-8°C
- pka
- 4.8 · 4.80±0.10(Predicted)
- Odor
- 0.1 % · at 0.10 % in propylene glycol. roasted burnt
- Odor Type
- milky
- Water Solubility
- soluble
- Henry's Law Constant
- 2.3 · 2.3×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Cosmetics Ingredients Functions
- FRAGRANCELIGHT STABILIZER
- LogP
- 0.72 · 0.720
- CAS DataBase Reference
- 3724 · 3724-65-0(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- -2 · (E)-2-BUTENOIC ACID
- FDA 21 CFR
- 175.105 · 175.105; 175.350; 176.170;176.180
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 5 WZZ4O5Q · YW5WZZ4O5Q
- NIST Chemistry Reference
- Crotonic acid(3724-65-0)
- EPA Substance Registry System
- Crotonic acid (3724-65-0)
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 21 · NA.21
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 302 · H302-H312-H314
- Precautionary statements
- 264 · P264-P270-P280-P260-P301+P312-P330-P302+P352-P312-P362+P364-P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P305+P351+P338-P405-P501
- Hazard Codes
- C
- Risk Statements
- 21 · 21/22-34
- Safety Statements
- 26 · 26-36/37/39-45
- RIDADR
- 2823 · UN 2823
- WGK Germany
- 3 · 3
- RTECS
- 2900000 · GQ2900000
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- III
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 4 DermalSkin · Acute Tox. 4 DermalSkin Corr. 1B
- Hazardous Substances Data
- 3724 · 3724-65-0(Hazardous Substances Data)
Safety & regulation
GHS classification
GHS Classification
Danger
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- GQ2900000
- ridadr
- UN 2823
- risk_code
- 21/22-34
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- C
- safety_code
- 26-36/37/39-45
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- III
- Hazard statements
- H302-H312-H314
- Hazard Classifications
- Acute Tox. 4 DermalSkin Corr. 1B
- Precautionary statements
- P264-P270-P280-P260-P301+P312-P330-P302+P352-P312-P362+P364-P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P305+P351+P338-P405-P501
- Hazardous Substances Data
- 3724-65-0(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
DescriptionCrotonic acid is a white or colorless, crystalline solid with a pungent odor. May be transported as amolten liquid. Molecular weight=86.10; Boilingpoint=187-189℃; Freezing/Melting point=72℃; Flashpoint=88℃ (oc); Autoignition temperature=396℃.Hazard Identification (based on NFPA-704 M RatingSystem): Health 3, Flammability 2, Reactivity 0. Soluble inwater; solubility=9% at 25℃. This chemical is the commercially used trans-isomer. The cis-isomer is lessstable and melts at 15℃.
UsesSynthesis of resins, polymers, plasticizers, drugs.
UsesCrotonic acid is used in the synthesis of resins, polymers, plasticizers, and drugs. It is also used as a softening agent for synthetic rubber and in medicinal chemicals.
General DescriptionA white crystalline solid. Shipped as either a solid or liquid. Melting point 59°F. Soluble in water and less dense than water. Flash point 190°F. Corrosive to metals and tissue.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
广州纳珑化工有限公司13192879270; 13192879270 · [email protected]
Hong Kong Tiansheng New Material Trading Co., Ltd+8617320695765 · [email protected]
武汉吉业升化工有限公司027-83360216 18040558719 · [email protected]
山东前元高分子材料有限公司18678041314 18765609661 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Hangzhou Verychem Science And Technology Co.Ltd+86-86-57188162785 +8613606544505 · [email protected]
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江苏普乐司生物科技有限公司0513-66017706 18551496367 · [email protected]
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南京维奥化工有限公司Please Send Email 18652950785 · [email protected]
南京瑞泰生化技术有限公司+86-(0)25-84931986,(0)18951962398
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上海蓝润化学有限公司021-69515658 ; 69515628 13701998368 · [email protected]
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天津荣燊化工有限公司18317763565; 18317763565 · [email protected]
深圳振强药物研发有限公司+86-0755-66853366 +86-13670046396 · [email protected]
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Additional notes
DefinitionExists in cis and trans isomeric forms, the latter being the stable isomer used commercially. The cis form melts at 15C and is sometimes called isocrotonic acid.
Related reactions
2 records
Compound notes
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