W284300

Sigma-Aldrich

4-Pentenoic acid

≥98%, stabilized, FG

Synonym(s):
3-Vinylpropionic acid, Allylacetic acid
Linear Formula:
CH2=CHCH2CH2COOH
CAS Number:
Molecular Weight:
100.12
FEMA Number:
2843
Beilstein/REAXYS Number:
1633696
EC Number:
Council of Europe no.:
2004
MDL number:
PubChem Substance ID:
Flavis number:
8.048
NACRES:
NA.21
Pricing and availability is not currently available.

Quality Level

biological source

synthetic

grade

FG
Halal
Kosher

Agency/Method

meets purity specifications of JECFA

reg. compliance

EU Regulation 1334/2008 & 178/2002
FDA 21 CFR 172.515

vapor density

>1 (vs air)

assay

≥98%

contains

α-tocopherol, synthetic as stabilizer

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.)

Documentation

see Safety & Documentation for available documents

Organoleptic

cheese

food allergen

no known allergens

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

4-Pentenoic acid is a volatile acid reported to be found in tobacco.

Other Notes

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Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

C

Risk Statement

22-34

Safety Statement

26-36/37/39-45

RIDADR

UN 1760 8 / PGII

WGK Germany

WGK 1

Flash Point(F)

192.2 °F - closed cup

Flash Point(C)

89 °C - closed cup

Steam volatile acids of Latakia tobacco leaf.
Creasy PJ & Saxby MJ.
Phytochemistry, 8(12), 2427-2429 (1969)
Effects of flue-curing and ageing on the volatile, neutral and acidic constituents of Virginia tobacco.
Wahlberg I, et al.
Phytochemistry, 16(8), 1217-1231 (1977)
W Tang et al.
Chemical research in toxicology, 8(5), 671-682 (1995-07-01)
It is postulated that the hepatotoxicity of valproic acid (VPA) results from the mitochondrial beta-oxidation of its cytochrome P450 metabolite, 2-propyl-4-pentenoic acid (4-ene VPA), to 2-propyl-(E)-2,4-pentadienoic acid ((E)-2,4-diene VPA) which, in the CoA thioester form, either depletes GSH or produces...
K Kassahun et al.
Drug metabolism and disposition: the biological fate of chemicals, 21(6), 1098-1106 (1993-11-01)
The terminal olefin metabolite of valproic acid (VPA), 4-ene VPA, is an analog of the experimental hepatotoxin 4-pentenoic acid and is believed to play a role in the hepatotoxicity of VPA. The formation of glutathione and N-acetylcysteine conjugates of the...
Y Boulanger et al.
Magnetic resonance in medicine, 28(1), 137-144 (1992-11-01)
The metabolism of 4-pentenoate in isolated kidney tubules has been investigated by 1H and 13C NMR. The 4-pentenoate metabolite, 3-keto-4-pentenoyl-CoA, accumulated in proximal tubules only and its formation could be competitively inhibited by octanoate. 4-Pentenoate was metabolized in thick ascending...

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