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419133

Sigma-Aldrich

Pentadecanolide

98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C15H28O2
CAS Number:
106-02-5
Molecular Weight:
240.38
Beilstein:
143710
EC Number:
203-354-6
MDL number:
MFCD00039667
UNSPSC Code:
12352100
PubChem Substance ID:
24866093
NACRES:
NA.22

Assay

98%

form

solid

bp

137 °C/2 mmHg (lit.)

mp

34-38 °C (lit.)

density

0.918 g/mL at 25 °C (lit.)

functional group

ester

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

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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
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBL0618
STBC7792V
S36576
S35531
09306DE

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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)

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