Skip to Content
MilliporeSigma
All Photos(2)

Documents

419133

Sigma-Aldrich

Pentadecanolide

98%

Synonym(s):

1-Oxa-2-cyclohexadecanone, 15-Hydroxypentadecanoic acid lactone, 15-Pentadecanolide, Pentalide

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C15H28O2
CAS Number:
Molecular Weight:
240.38
Beilstein:
143710
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

98%

form

solid

bp

137 °C/2 mmHg (lit.)

mp

34-38 °C (lit.)

density

0.918 g/mL at 25 °C (lit.)

SMILES string

O=C1CCCCCCCCCCCCCCO1

InChI

1S/C15H28O2/c16-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-17-15/h1-14H2

InChI key

FKUPPRZPSYCDRS-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

General description

Pentadecanolide (PDL) is a 16-membered ring lactone. Its anionic polymerization by employing potassium alkoxides as initiator has been reported. It has been reported as a potential selective inhibitors of rat liver cyclic AMP-dependent protein kinase (cAK) [IC50 value = 20μM]. Synthesis of PDL in overall yield of 60%, using 2-nitrocyclododecanone as starting reagent, has been described.

Application

Pentadecanolide may be used for the synthesis of poly(pentadecanolide) (PPDL) by Novozyme 435 catalyzed ring-opening polymerization. It may be employed as starting reagent for the synthesis of terminally-branched iso-fatty acids (iso-C15-C17).

Pictograms

Environment

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

320.0 °F - closed cup

Flash Point(C)

160 °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’.

Already Own This Product?

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

Visit the Document Library

Anionic polymerization of pentadecanolide. A new route to potentially biodegradable aliphatic polyester.
Jedlinski Z, et al.
Macromolecular Chemistry and Physics, 197(9), 1923-1929 (1996)
B H Wang et al.
Phytochemistry, 41(1), 55-63 (1996-01-01)
A set of plant- and animal-derived amphiphilic triterpenoids have been shown to be potent and selective inhibitors of the catalytic subunit of rat liver cyclic AMP-dependent protein kinase (cAK). Thus plant-derived 18 alpha- and 18 beta-glycyrrhetinic acid, ursolic acid, oleanolic
Effect of reaction temperature on the physicochemical properties of poly (pentadecanolide) obtained by enzyme-catalyzed ring-opening polymerization.
Wilberth H-K, et al.
Polymer Bull., 72(3), 1-12 (2015)
Mark B Richardson et al.
Beilstein journal of organic chemistry, 9, 1807-1812 (2013-09-26)
A gram-scale synthesis of terminally-branched iso-fatty acids (iso-C12-C19) was developed commencing with methyl undec-10-enoate (methyl undecylenate) (for iso-C12-C14) or the C15 and C16 lactones pentadecanolide (for iso-C15-C17) and hexadecanolide (for iso-C18-C19). Central to the approaches outlined is the two-step construction
A short synthesis of 15-pentadecanolide.
Stanchev S, et al.
Tetrahedron Letters, 34(38), 6107-6108 (1993)

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