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245925

Sigma-Aldrich

4-Pentenoic acid

97%

Synonym(s):

3-Vinylpropionic acid, Allylacetic acid

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About This Item

Linear Formula:
CH2=CHCH2CH2COOH
CAS Number:
591-80-0
Molecular Weight:
100.12
Beilstein:
1633696
EC Number:
209-732-7
MDL number:
MFCD00004408
UNSPSC Code:
12352100
PubChem Substance ID:
24854769
NACRES:
NA.22

vapor density

>1 (vs air)

Assay

97%

form

liquid

refractive index

n20/D 1.428 (lit.)

bp

83-84 °C/12 mmHg (lit.)

mp

−22.5 °C (lit.)

density

0.981 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

OC(=O)CCC=C

InChI

1S/C5H8O2/c1-2-3-4-5(6)7/h2H,1,3-4H2,(H,6,7)

InChI key

HVAMZGADVCBITI-UHFFFAOYSA-N

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General description

The sulfonation of 4-pentenoic acid (Allylacetic acid) yields the corresponding γ-lactone.

Application

4-Pentenoic acid (Allylacetic acid) was used to inhibit fatty acid oxidation in rat heart mitochondria.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

192.2 °F - closed cup

Flash Point(C)

89 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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On the rate-determining step of fatty acid oxidation in heart. Inhibition of fatty acid oxidation by 4-pentenoic acid.
J C Fong et al.
The Journal of biological chemistry, 253(19), 6917-6922 (1978-10-10)
Selina Schimka et al.
The Journal of chemical physics, 147(3), 031101-031101 (2017-07-25)
Here we report on a light triggered remote control of microgel size in the presence of photosensitive surfactant. The hydrophobic tail of the cationic surfactant contains azobenzene group that undergoes a reversible photo-isomerization reaction from a trans- to a cis-state
Rec. Trav. Chim., 111, 478-478 (1992)
Daniel C Whitehead et al.
Journal of the American Chemical Society, 132(10), 3298-3300 (2010-02-23)
A reagent controlled organocatalytic enantioselective chlorolactonization reaction has been developed. Several 4-aryl pentenoic acids were cyclized in the presence of 0.1 equiv of (DHQD)(2)PHAL, employing various N-chlorinated hydantoins as the terminal chlorenium source. Ten examples are presented with selectivities ranging
Y Boulanger et al.
Renal physiology and biochemistry, 16(4), 182-202 (1993-07-01)
4-Pentenoate (4P) is a short-chain fatty acid which causes a complete renal Fanconi syndrome. We have examined the mechanism of 4P toxicity along the nephron after a prolonged (30 min) exposition of isolated renal tubular segments to this agent. In
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