Skip to Content
MilliporeSigma
All Photos(3)

Key Documents

471801

Sigma-Aldrich

4-Pentenoic anhydride

98%

Sign Into View Organizational & Contract Pricing


About This Item

Linear Formula:
(H2C=CHCH2CH2CO)2O
CAS Number:
Molecular Weight:
182.22
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

98%

refractive index

n20/D 1.447 (lit.)

bp

78-81 °C/0.4 mmHg (lit.)

density

0.997 g/mL at 25 °C (lit.)

functional group

allyl
anhydride
ester

SMILES string

C=CCCC(=O)OC(=O)CCC=C

InChI

1S/C10H14O3/c1-3-5-7-9(11)13-10(12)8-6-4-2/h3-4H,1-2,5-8H2

InChI key

NEDHQDYBHYNBIF-UHFFFAOYSA-N

General description

4-Pentenoic anhydride is a carboxylic anhydride.

Application

4-Pentenoic anhydride may be used:
  • In the preparation of glucose functionalized (co)polymers.
  • As a monomer in the preparation of cross-linked polyanhydrides.
  • For the preparation of polymers with pendant vinyl or acetylene.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

2-(Trimethylsilyl) ethyl Glycosides. Transformation into the Corresponding 1-O-Acyl Sugars.
Ellervik U and Magnusson G.
Acta Chemica Scandinavica, 47, 826-826 (1993)
Studies of the mechanism of the hypoglycemic action of 4-pentenoic acid.
Corredor C, et al.
Proceedings of the National Academy of Sciences of the USA, 58(6), 2299-2299 (1967)
Gaojian Chen et al.
Chemical communications (Cambridge, England), (10)(10), 1198-1200 (2009-02-26)
Homopolymer and block copolymer bearing carbohydrate side chain functionality were obtained by grafting glucothiose onto alkene functional scaffolds via a thiol-ene click reaction and the resulting copolymer was used to form thermo-responsive micelles as a potential drug carrier.
Katie L Poetz et al.
Biomacromolecules, 15(7), 2573-2582 (2014-05-23)
Several critical aspects of cross-linked polyanhydrides made using thiol-ene polymerization are reported, in particular the erosion, release, and solution properties, along with their cytotoxicity toward fibroblast cells. The monomers used to synthesize these polyanhydrides were 4-pentenoic anhydride and pentaerythritol tetrakis(3-mercaptopropionate).
Vien T Huynh et al.
Biomacromolecules, 12(5), 1738-1751 (2011-04-12)
Statistical and block copolymers based on poly(2-hydroxyethyl methacrylate) (PHEMA) and poly[oligo(ethylene glycol) methylether methacrylate] (POEGMEMA) were modified with 4-pentenoic anhydride or 4-oxo-4-(prop-2-ynyloxy)butanoic anhydride to generate polymers with pendant vinyl or acetylene, respectively. Subsequent thiol-ene or thiol-yne reaction with thioglycolic acid

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service