All Photos(2)
Synonym(s):
1-Oxa-2-cyclohexadecanone, 15-Hydroxypentadecanoic acid lactone, 15-Pentadecanolide, Pentalide
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
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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
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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).
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Acute 1 - Aquatic Chronic 2
WGK
WGK 1
Flash Point(F)
320.0 °F
Flash Point(C)
160 °C
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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)
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
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)
A short synthesis of 15-pentadecanolide.
Stanchev S, et al.
Tetrahedron Letters, 34(38), 6107-6108 (1993)
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