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Safety Information

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

Quality Level

100

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

JAN Code

419133-25G:
419133-BULK:
419133-100G:
419133-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
STBC7792V
S36576
S35531
09306DE
01904PC

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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
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)
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)
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
A short synthesis of 15-pentadecanolide.
Stanchev S, et al.
Tetrahedron Letters, 34(38), 6107-6108 (1993)

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