Hexadecen-16-olide ambrettolide

Ambrettolide is an unsaturated cyclic lactone, which readily undergoes ROMP to an unsaturated linear polyester (A/ — 95 000) in the presence of WCl6/Me4Sn (Ast 1976b, 1977a). 

---

The constituents responsible for the musk odor of the oil are (Z)-7-hexadecen-16-olide [123-69-3] (ambrettolide) and (Z)-5-tetradecen-14-olide [63958-52-1]. ... 

Macrocyclic lactones like ambrettolide (7-hexadecen-l,16-olide) 158, 15-pentadecanolide (cyclopentadecanolide) 159, hexadecanolide (cyclohexa-decanolide) 160 and cyclohexadec-7-enolide 161 (Structure 4.48) are called musks. They are found in a variety of essential oils, e.g. ambrette seed oil and angelica root oil [1-4, 21-23, 62]. 

Ci6H2g02, Mt 252.40, is not reported as being found in nature, in contrast to (Z)-7-hexadecen-16-olide, which occurs in ambrette seed oil (see p. 182) and which is also referred to as ambrettolide. It is a colorless to slightly yellow liquid, re 0 0.949 -0.957, re 0 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... 

Hexadecenolide 6-Hexadecen-16-olide 7-Hexadec-7-en-16-olide. See Ambrettolide... 

Macrocyclic lactones such as ambrettolide (= 7-hexadecen-l,16-olide) (19), 15-pen-tadecanolide (20), hexadecanolide (21), and so on, as well as coumarin (22), dihydro-coumarin (23), bergaptene (24) nepetalactones (25) phthalides such as 3-butylphthahde (26), sedanolide (27), (Z)-ligustilide (28), 3-butyhdene-4,5-dihydrophthalide (29), and... 

Compounds isolated from the seed oil include ambrettolide, (Z)-7-hexadecen-16-olide), am-brettolic acid, and farnesol as well as 12,13-epoxyoleic acid, malvalic acid, sterculic acid, and C10-C18 acids (oleic, palmitic, Cio, C12, Ci4, C16, Cis). (Z)-5-Tetradecen-14-olide, (Z)-5-dodecenyl acetate, and (Z)-5-tetradece-nyl acetate were isolated from the absolute in yields of 0.5%, 0.01%, and 0.4%, respectively in addition, 2-fra j, 6-ira j -famesylacetate, 2-cw,6-fra 5-famesylacetate, andoxacyclono-nadec-lO-en-2-one (an ambrettolide homo-logue) were found in the seed coat. The floral musky odor of the oil is primarily the result of ambrettolide and (Z)-5-tetradecen-14-olide. ... 

---