28645-51-4

Basic information

• Product Name: AMBRETTOLIDE
• Synonyms: AMBRETTOLIDE;16-HYDROXY-7-HEXADECENOIC ACID O-LACTONE;HEXADECEN-8-OLIDE;FEMA 2555;OMEGA-6-HEXADECENLACTONE;Oxacycloheptadec-10-en-2-on;16-Hydroxy-9-hexadecenoic acid lactone;1-Oxacycloheptadeca-10-en-2-one
• CAS NO: 28645-51-4
• Molecular Formula: C₁₆H₂₈O₂
• Molecular Weight: 252.39
• EINECS: 231-929-1
• Mol File: 28645-51-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 185-190 °C16 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.956 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.39E-06mmHg at 25°C
• Refractive Index: n20/D 1.479(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Methanol (Sparingly)
• Water Solubility: 15μg/L at 25℃
• CAS DataBase Reference: AMBRETTOLIDE(CAS DataBase Reference)
• NIST Chemistry Reference: AMBRETTOLIDE(28645-51-4)
• EPA Substance Registry System: AMBRETTOLIDE(28645-51-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-36
• WGK Germany: 2
• Hazardous Substances Data: 28645-51-4(Hazardous Substances Data)

Usage

Chemical Properties

AMBRETTOLIDE is not reported as being found in nature, in contrast to (Z)-7-hexadecen-16-olide, which occurs in ambrette seed oil and which is also referred to as ambrettolide. It is a colorless to slightly yellow liquid, d204 0.949–0.957, n20D 1.477–1.482, with an intense and powerful musk odor. It is prepared by treating aleuritic acid (9,10,16-trihydroxyhexadecanoic acid) with trimethyl orthoformate to give a dioxolane derivative. Reaction with acetic anhydride yields ??-acetoxy (E)-9-hexadecenoic acid methyl ester. This is lactonized with potassium hydroxide to give the title compound .

Occurrence

Found in oil of ambrette seed[Givaudan Index, 1961).

Uses

Ambrettolide is a macrocyclic lactone that naturally occurs in ambrette seed oil. Ambrettolide is nontoxic, has a musky odour, and is commonly used as a fixative in perfume formulations.

Preparation

From bromohexadecenoic acid(Bedoukian, 1967).

Flammability and Explosibility

Notclassified

InChI:InChI=1/C16H28O2/c17-16-14-12-10-8-6-4-2-1-3-5-7-9-11-13-15-18-16/h1,3H,2,4-15H2/b3-1-

Upstream product

• 1619-68-7 16-hydroxy-9-hexadecenoic acid 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 112-80-1 cis-Octadecenoic acid 
• 533-87-9 DL-threo-9RS,10RS,16-trihydroxyhexadecanoic acid 
• 210229-82-6 (E)-16-Chloro-hexadec-9-enoic acid methyl ester 
• 78924-81-9 methyl 16-hydroxy-(E)-9-hexadecenoate 
• 97944-69-9 threo-9,10-dihydroxyheptadecan-16-olide 
• 533-87-9 threo-9,10,16-trihydroxyhexadecanoic acid 
• 210229-83-7 16-chloro-(E)-9-hexadecenoic acid 
• 111017-63-1 2-Dimethylamino-tetradecahydro-1,3,10-trioxa-cyclopentacycloheptadecen-11-one 
• 6949-98-0 9,10,16-trihydroxyhexadecanoic acid 
• 25601-41-6 methyl 9-decenoate 
• 5048-35-1 oct-7-en-1-yl acetate 

Downstream Products

• 109-29-5 15-hexadecanolide 
• 24534-96-1 16-Hydroxypalmitinsaeurehydrazid 

Relevant articles and documents

Synthesis of (9E)-isoambrettolide, a macrocyclic musk compound, using the effective lactonization promoted by symmetric benzoic anhydrides with basic catalysts

Two alternative methods for the synthesis of (9E)-isoambrettolide are established via the rapid lactonization of the free threo-aleuritic acid or its protected seco-acid using substituted benzoic anhydrides with basic catalysts. The most efficient lactoni

At Long Last: Olefin Metathesis Macrocyclization at High Concentration

Macrocyclic lactones, ketones, and ethers can be obtained in the High-Concentration Ring-Closing Metathesis (HC-RCM) reaction in high yield and selectivity at concentrations 40 to 380 times higher than those typically used by organic chemists for similar macrocyclizations. The new method consists of using tailored ruthenium catalysts together with applying vacuum to distill off the macrocyclic product as it is formed by the metathetical backbiting of oligomers. Unlike classical RCM, no large quantities of organic solvents are used, but rather inexpensive nonvolatile diluents, such as natural or synthetic paraffin oils. Moreover, use of a protecting atmosphere or a glovebox is not needed, as the new catalysts are perfectly moisture and air stable. In addition, some other cyclic compounds previously reported as unobtainable by RCM in neat conditions, or in high dilutions even, can be formed with the help of the HC-RCM method.

METHOD FOR PRODUCING OMEGA-HYDROXY FATTY ACID ESTER AND PRECURSOR COMPOUND THEREOF

Provided is a method for producing a compound represented by Formula (III) while the production of by-products due to, for example, dimerization of a raw material or isomerization of a double bond position is suppressed. The method is a method for producing omega-hydroxy fatty acid ester and a precursor compound thereof of Formula (III), in which an alcohol derivative and a carboxylic acid derivative are subjected to a metathesis reaction in the presence of a catalyst to obtain a compound of Formula (III), wherein the alcohol derivative is at least one selected from the group consisting of a compound of Formula (VI) and a compound of Formula (I), and the carboxylic acid derivative is at least one selected from the group consisting of a compound of Formula (VII) and a compound of Formula (II), wherein the case where the alcohol derivative is formed of a compound of Formula (I) and the carboxylic acid derivative is formed of a compound of Formula (II) is excluded,