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389579

Sigma-Aldrich

δ-Valerolactone

technical grade

Synonym(s):

delta-Valerolactone, Tetrahydro-2H-2-pyranone

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About This Item

Empirical Formula (Hill Notation):
C5H8O2
CAS Number:
542-28-9
Molecular Weight:
100.12
Beilstein:
106436
EC Number:
208-807-1
MDL number:
MFCD00006645
UNSPSC Code:
12352100
PubChem Substance ID:
24864292
NACRES:
NA.22

grade

technical grade

form

liquid

impurities

<25% polymer

refractive index

n20/D 1.457 (lit.)

bp

226-229 °C (lit.)
58-60 °C/0.5 mmHg (lit.)

mp

−13-−12 °C (lit.)

density

1.079 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

O=C1CCCCO1

InChI

1S/C5H8O2/c6-5-3-1-2-4-7-5/h1-4H2

InChI key

OZJPLYNZGCXSJM-UHFFFAOYSA-N

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Application

δ-Valerolactone (tetrahydro-2H-2-pyranone or δ VL) can be used as a monomer unit in the synthesis of poly(δ-valerolactone)s poly(conjugated ester)s via ring-opening polymerization.
It can also be used as a starting material in the synthesis of (+)-guadinomic acid , sodium δ-hydroxyvalerate , methyl δ-hydroxyvalerate , and 5-hydroxyvaleraldehyde.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

233.6 °F - closed cup

Flash Point(C)

112 °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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Alice E van der Ende et al.
Journal of the American Chemical Society, 130(27), 8706-8713 (2008-06-12)
We present the synthesis of discrete functionalized polyester nanoparticles in selected nanoscale size dimensions via a controlled intermolecular chain cross-linking process. The novel technique involves the controlled coupling of epoxide functionalized polyesters with 2,2'-(ethylenedioxy)bis(ethylamine) to give well-defined nanoparticles with narrow
Artificial molecular clamp: a novel device for synthetic polymerases.
Yoshinori Takashima et al.
Angewandte Chemie (International ed. in English), 50(33), 7524-7528 (2011-07-12)
Courtney L Millar et al.
Metabolic syndrome and related disorders, 16(9), 464-469 (2018-08-22)
High-density lipoprotein (HDL) particles are protective against atherosclerosis. However, HDL function is impaired in metabolic syndrome (MetS) due to low-grade inflammation and dyslipidemia. Foods containing polyphenols, such as grapes, may prevent HDL dysfunction via antioxidant or anti-inflammatory effects. We evaluated
Ryo Shintani et al.
Organic letters, 11(16), 3754-3756 (2009-07-30)
A new synthetic method of spirooxindole derivatives has been developed by way of a palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with isatins. By employing a newly prepared phosphoramidite ligand, the reaction proceeds smoothly with excellent diastereoselectivity. Preliminary results of its application
Synthesis of thymoquinone-artemisinin hybrids: new potent antileukemia, antiviral, and antimalarial agents
Frohlich T, et al.
ACS Medicinal Chemistry Letters, 9(6), 534-539 (2017)
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