Study of structural and electronic origin of ambergris odor of some compounds

Li, Cheng; Xu, Li; Mao, Hai F.; Wang, Gen Li

doi:10.1007/s00894-008-0363-3

Cited by 6 publications

(4 citation statements)

References 13 publications

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“…Therefore, it is considered a valuable fragrance ingredient. It should be noted that (−)-ambrafuran has a much stronger odor than its enantiomer (+)-ambrafuran, which has a relatively different odor [223][224][225]. Currently, in the perfume industry, ambrafurans are derived entirely from synthetic or semi-synthetic sources.…”

Section: Fragrance Of Marine Animalsmentioning

confidence: 99%

Occurrence of Marine Ingredients in Fragrance: Update on the State of Knowledge

et al. 2021

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The fragrance field of perfumes has attracted considerable scientific, industrial, cultural, and civilizational interest. The marine odor is characterized by the specific smell of sea breeze, seashore, algae, and oyster, among others. Marine odor is a more recent fragrance and is considered as one of the green and modern fragrances. The smells reproducing the marine environment are described due to their content of Calone 1951 (7-methyl-2H-1,5-benzodioxepin-3(4H)-one), which is a synthetic compound. In addition to the synthetic group of benzodioxepanes, such as Calone 51 and its derivatives, three other groups of chemical compounds seem to represent the marine smell. The first group includes the polyunsaturated cyclic ((+)-Dictyopterene A) and acyclic (giffordene) hydrocarbons, acting as pheromones. The second group corresponds to polyunsaturated aldehydes, such as the (Z,Z)-3,6-nonadienal, (E,Z)-2,6-nonadienal, which are most likely derived from the degradation of polyunsaturated fatty acids. The third group is represented by small molecules such as sulfur compounds and halogenated phenols which are regarded as the main flavor compounds of many types of seafood. This review exposes, most notably, the knowledge state on the occurrence of marine ingredients in fragrance. We also provide a detailed discussion on several aspects of essential oils, which are the most natural ingredients from various marine sources used in fragrance and cosmetics, including synthetic and natural marine ingredients.

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Section: Fragrance Of Marine Animalsmentioning

confidence: 99%

Occurrence of Marine Ingredients in Fragrance: Update on the State of Knowledge

et al. 2021

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“…Accordingly, it is considered as a high value, fine fragrant ingredient. Interestingly, (−)-ambrafuran presents a much stronger odor than its (+)-ambrafuran antipode with a somewhat different odor [ 8 , 9 ].…”

Section: Ambrafuran a High Value Fine Fragrant Perfume Ingredienmentioning

confidence: 99%

Ambrafuran (AmbroxTM) Synthesis from Natural Plant Product Precursors

2020

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Ambergris, an excretion product of sperm whales, has been a valued agent in the formulation of perfumes. The composition of ambergris consists of two major components: 40–46% cholestanol type steroids and approximately 25–45% of a triterpenoid known as ambrein. Ambergris undergoes oxidative decomposition in the environment to result in odorous compounds, such as ambraoxide, methylambraoxide, and ambracetal. Its oxidized form, ambrafuran (IUPAC name: 3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran), is a terpene furan with a pleasant odor and unique olfactive and fixative properties. The current state of the fragrance industry uses ambrafuran materials entirely from synthetic or semisynthetic sources. However, natural compounds with the potential to be converted to ambergris-like odorants have been extracted from several different types of plants. Here we review plant terpenoids suitable as starting materials for the semisyntheses of ambrafuran or intermediates, such as ambradiol, that can be used in biocatalytic transformations to yield ambrafuran.

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“…Because of the limited supply of Ambergris and its relatively high cost, synthetic alternatives have been considered. A particularly effective synthetic fixative substitute, is Ambrox ((−)-8α-12-dihydroxy-13,14,15,16-tetranorlabdane). , The chemical structure is shown in Figure .…”

Section: Introductionmentioning

confidence: 99%

“…A particularly effective synthetic fixative substitute, is Ambrox ((−)-8α-12-dihydroxy-13,14,15,16-tetranorlabdane). 2,3 The chemical structure is shown in Figure 1.…”

Section: ■ Introductionmentioning

confidence: 99%

A Multiobjective Optimization Approach for the Development of a Sustainable Supply Chain of a New Fixative in the Perfume Industry

Martínez-Guido

González-Campos

Río

et al. 2014

ACS Sustainable Chem. Eng.

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Ambrox is an important fixative used in the manufacture of perfumes. It is obtained through complex chemical synthesis routes with high costs. Recent research efforts at the Institute of Chemical and Biological Researches at the Universidad Michoacana have led to the one-step synthesis of Ambrox from extracts of Ageratina jocotepecana (an endemic plant of the State of Michoacán in Mexico). This new chemical route is attractive from a manufacturing perspective. However, there are several challenges for the industrial application of this plant and its incorporation in the supply chain of the perfume industry. This paper presents a multiobjective optimization approach for the development and assessment of the supply chain of Ageratina jocotepecana to account for its growth in current and reclaimed lands, distribution, processing to yield Ambrox, and distribution of products. The approach accounts for the economic, environmental, and social aspects and establishes systematic trade-offs. A case study is solved to consider the supply chain and the trade-offs of the multiple objectives.

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Study of structural and electronic origin of ambergris odor of some compounds

Cited by 6 publications

References 13 publications

Occurrence of Marine Ingredients in Fragrance: Update on the State of Knowledge

Occurrence of Marine Ingredients in Fragrance: Update on the State of Knowledge

Ambrafuran (AmbroxTM) Synthesis from Natural Plant Product Precursors

A Multiobjective Optimization Approach for the Development of a Sustainable Supply Chain of a New Fixative in the Perfume Industry

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