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21580

Sigma-Aldrich

Hexanoic anhydride

purum, ≥97.0% (GC)

Synonym(s):

Caproic anhydride

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About This Item

Linear Formula:
[CH3(CH2)4CO]2O
CAS Number:
2051-49-2
Molecular Weight:
214.30
Beilstein:
1776561
EC Number:
218-121-4
MDL number:
MFCD00009509
UNSPSC Code:
12352100
PubChem Substance ID:
329752175
NACRES:
NA.22

grade

purum

Quality Level

200

Assay

≥97.0% (GC)

form

liquid

refractive index

n20/D 1.428 (lit.)
n20/D 1.429

bp

246-248 °C (lit.)

solubility

ethanol: soluble 1 g/10 mL, clear, colorless

density

0.928 g/mL at 20 °C (lit.)

SMILES string

CCCCCC(=O)OC(=O)CCCCC

InChI

1S/C12H22O3/c1-3-5-7-9-11(13)15-12(14)10-8-6-4-2/h3-10H2,1-2H3

InChI key

PKHMTIRCAFTBDS-UHFFFAOYSA-N

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Application

Hexanoic anhydride has been used in:
  • green synthesis of esters of acyclovir (acyclovir prodrugs)
  • preparation of hexanoyl-modified chitosan nanoparticles and chitosan-based polymeric surfactants via N-acylation of chitosans

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCB7907
BCCB2606
BCBW3585
BCBW3584
BCBV2183

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Moo-Yeal Lee et al.
International journal of biological macromolecules, 36(3), 152-158 (2005-07-14)
Chitosan-based polymeric surfactants (CBPSs) were prepared by N-acylation of chitosans (chitosan 10 and 500) with several acid anhydrides such as hexanoic (C6), lauric (C12), and palmitic (C16) anhydrides. Among the CBPS samples, CBPSs having a good solubility at pH 4.0
Rubén de Regil-Hernández et al.
Chemical & pharmaceutical bulletin, 59(9), 1089-1093 (2011-09-02)
Different green synthesis of alkyl esters of acyclovir (acyclovir prodrugs) is described. Hexanoic, decanoic, dodecanoic and tetradecanoic acyclovir esters were synthesized reacting acyclovir and the respective acid anhydride in dimethyl sulfoxide (DMSO), in solvents from renewable sources and without solvent
Kashappa Goud Desai et al.
Drug delivery, 13(5), 375-381 (2006-08-01)
Hexanoyl chitosan was synthesized through a coupling reaction between chitosan and hexanoic anhydride. Proton nuclear magnetic resonance (1HNMR) and fourier-transform infrared (FTIR) spectroscopy studies showed the formation of hexanoyl chitosan. The nanoparticles of hexanoyl chitosan were prepared through ionotropic gelation
Marco Igor Valencia-Sánchez et al.
Molecular cell, 74(5), 1010-1019 (2019-04-15)
The essential histone H3 lysine 79 methyltransferase Dot1L regulates transcription and genomic stability and is deregulated in leukemia. The activity of Dot1L is stimulated by mono-ubiquitination of histone H2B on lysine 120 (H2BK120Ub); however, the detailed mechanism is not understood.
Anna Pensalfini et al.
Cell reports, 33(8), 108420-108420 (2020-11-26)
Neuronal endosomal dysfunction, the earliest known pathobiology specific to Alzheimer's disease (AD), is mediated by the aberrant activation of Rab5 triggered by APP-β secretase cleaved C-terminal fragment (APP-βCTF). To distinguish pathophysiological consequences specific to overactivated Rab5 itself, we activate Rab5

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