Cyclopentadecanolide

Cyclopentadecanolide Basic information
Product Name:Cyclopentadecanolide
Synonyms:15-HYDROXYPENTADECANOIC ACID LACTONE;Cyclopentadecanolide~15-Hydroxypentadecanoic acid lactone~omega-Pentadecalactone;OMEGA-PENTADECALACTONE 98+%;exaltolid;CYCLOPENTADECENOLIDE;Pentadecan-15-olid;Exaltolide, Oxacyclohexadecan-2-one;CYCLOPENTADECANOLIDE (OXACYCLOHEXADECAN-2-ONE)
CAS:106-02-5
MF:C15H28O2
MW:240.38
EINECS:203-354-6
Product Categories:Biochemicals and Reagents;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Fatty Acids and conjugates;Fatty Acyls;Lactones;Lipids;Organic Building Blocks;Others;Saturated Fatty Acids and Derivatives
Mol File:106-02-5.mol
Cyclopentadecanolide Structure
Cyclopentadecanolide Chemical Properties
Melting point 34-38 °C(lit.)
Boiling point 137 °C2 mm Hg(lit.)
density 0.918 g/mL at 25 °C(lit.)
vapor pressure 0.085Pa at 25℃
FEMA 2840 | OMEGA-PENTADECALACTONE
refractive index 1.4700
Fp >230 °F
storage temp. Sealed in dry,Room Temperature
solubility Chloroform, Ethyl Acetate, Methanol (Slightly)
form Solid
color White to Off-White
Odorat 10.00 % in dipropylene glycol. musk animal powdery natural fruity
Odor Typemusk
Water Solubility Soluble in alcohol, dipropylene glycol. Insoluble in water.
Merck 14,3910
JECFA Number239
BRN 143710
LogP5.79 at 25℃
CAS DataBase Reference106-02-5(CAS DataBase Reference)
NIST Chemistry ReferenceOxacyclohexadecan-2-one(106-02-5)
EPA Substance Registry SystemOxacyclohexadecan-2-one (106-02-5)
Safety Information
Safety Statements 24/25
WGK Germany 1
RTECS RN9775000
TSCA Yes
HS Code 29322090
toxicityBoth the acute oral LD50 value in rats and the acute dermal LD50 value in rabbits exceeded 5 g/kg (Levenstein, 1974).
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
Cyclopentadecanolide Usage And Synthesis
Chemical Propertieswhite crystalline low melting solid
Chemical PropertiesCyclopentadecanolide occurs in small quantities in, for example, angelica root oil. It forms colorless crystals (mp 37–38°C) with a delicate, musk-like odor.
Chemical Propertiesω-Pentadecalactone has an extraordinarily persistent, musk-like odor.
OccurrenceOriginally reported found in the essential oil from angelica roots.
UsesAs a fixative in perfumery.
UsesPentadecanolide is a monomer used to make PGA-co-pentadecalactone polymers to be used in the development of directly compressed prolonged release tablets of slightly soluble drugs such as ketoprofen.
UsesPentadecanolide 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).
DefinitionChEBI: Cyclopentadecanolide is a macrolide.
PreparationThe main industrial syntheses start from compounds produced from cyclododecatriene: either by ring expansion of cyclododecanone or by depolymerization of polyesters of 15-hydroxypentadecanoic acid (from 1,12-dodecanediol).
Aroma threshold valuesDetection: 1 to 4 ppb
Taste threshold valuesTaste characteristics at 75 ppm: vanilla bean, powdery helioropine, creamy and licorice.
Synthesis Reference(s)Tetrahedron Letters, 34, p. 6107, 1993 DOI: 10.1016/S0040-4039(00)61741-0
The Journal of Organic Chemistry, 50, p. 2394, 1985 DOI: 10.1021/jo00213a044
General DescriptionPentadecanolide is one of the major components, isolated from the root of Angelica archangelica L., species. It is a synthetic musk, which exists as a widespread contaminant in the environment.
Flammability and ExplosibilityNonflammable
Trade nameMacrolide® (Symrise), Exaltolide®, Exaltolide®Total (Firmenich), Pentalide (Soda Aromatic).
Purification MethodsIt has been recrystallised from MeOH (4 parts) at -15o. [Hundieck
BENZOYLHETERATISINE HYDROCHLORIDE Epothilone B Hyaluronic acid ε-Caprolactone TRIOXSALEN 5 ALPHA-ANDROSTAN-17 BETA-CARBOXYLIC ACID-11 BETA,18-EPOXY-18-OL-3-ONE GAMMA-LACTONE Ethyl 2-(Chlorosulfonyl)acetate Cyclopentadecanone 5ALPHA-ANDROSTAN-17BETA-CARBOXYLIC ACID-3BETA,18-DIOL-11BETA,18-EPOXY GAMMA LACTONE Ascoric Acid Folic acid Sagopilone heteratisine 4-ANDROSTEN-18-AL-17BETA-CARBOXYLIC ACID-11BETA-OL-3-ONE-(18-11)-HEMIACETAL-(20->8)-LACTONE Epothilone A Cyclopentadecanolide Spironolactone Citric acid

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