Table 1. Authors cited more than 3 times in entries in Beilstein for analytical or synthetic work on ambergris, ambrox and ambrein.
Dictionary of Organic Compounds -
Name: Ambrein CAS Reg. No: 473-03-0 Formula: C30H52O Weight: 428.740 Cmpd. Type: Ambrein group Source: Constituent of ambergris. State: Cryst. Mp: 82-83 deg C Opt. Rotation: +14.1 deg (c, 1 in C6H6), wavelength Na line
Name: Dodecahydro-3a,6,6,9a-tetramethylnaphtho(2,1-b)furan; 9CI Synonyms: 1,1,4a,6-Tetramethyl-5-ethyl-6,5-oxidodecahydronaphthalene; Bicyclofarnesyl epoxide CAS Reg. No: 6790-58-5 Formula: C16H28O Weight: 236.397 Cmpd. Type: Labdanes Source: Volatile constit. of Ambergris tincture. Use: Important amber perfumery ingredient. Compound 1: Dodecahydro-3a,6,6,9a-tetramethylnaphtho(2,1-b)furan, (3aa,5ab,6a,9aa,9bb)-form Synonyms: Ambroxide; Ambrox; Dodecahydro-3a,6,6,9a-tetramethylnaphtho(2,1-b)furan, n-Epoxide CAS Reg. No: 6790-58-5 Source: Constituent of ambergris. State: Crystals from petroleum ether. Mp: 75-76 C. Compound 2: Dodecahydro-3a,6,6,9a-tetramethylnaphtho(2,1-b)furan, (3aa,5aa,9aa,9ba)-form Synonyms: Isoambrox; Dodecahydro-3a,6,6,9a-tetramethylnaphtho(2,1-b)furan, Isoepoxide CAS Reg. No: 68365-88-8 Mp: 60 C.
The Kirk-Othmer Encyclopedia of Chemistry -
Ambergris is an accumulation of material originating in the intestine of the whale, but today is obtained during processing of the whale carcass. Ambergris has to be aged before it is useful to perfumers. The main constituent of ambergris is the alcohol, ambrein [473-03-0], which upon exposure to light and air oxidizes to form, among other odoriferous products, very valuable amber and floral lactones, aldehydes, and ketones. Today, ambergris has been replaced by synthetic products in the perfume industry.
Ambergris - CAS Registry Number 8038-65-1
Concretion from intestinal tract of the sperm whale, Physeter catodon L., Physeteridae. Found in tropical seas or seashores. Perfumers have used ambergris for centuries for its desirable odoriferous and fixative properties. Three major components isolated are the triterpene alcohol ambrein, epicoprostanol and coprostanone: Ruzicka, Lardon, Helv. Chim. Acta 29, 912 (1946); Lederer et al., ibid., 1354; Hardwick, Laws, The Analyst 76, 662 (1951). Ambergris falls under the Marine Mammal Protection Act of 1972 and is illegal to import in the U.S.A. Analytical method for the detection and identification of ambergris: T. F. Governo et al., J. Assoc. Offic. Anal. Chem. 60, 160 (1977). Hypothesis on the biological origin of ambergris: P. A. Dubois, Parfums, Cosmet., Arome 19, 35 (1978).
A gray to black, waxy mass; characteristic odor. Density 0.8-0.92. Melting point about 60 degrees; flammable; almost completely volatile by heat. Insoluble in water or in alkali hydroxides; soluble in hot alcohol, chloroform, ether, fats, volatile oils. Used chiefly in perfumery as tincture and essence for fixing delicate odors.
History of Perfumery -
The actual mixing or blending of perfumes is first discussed by Theophrastus, 370BC, whose writings show that the art form was already well advanced. The Arabs in developing their trade routes introduced the precious, and still today exotic, ambergris from the sperm whale, sandalwood from India and clove buds and patchouli from Malaya. In turn, these and other products of the Middle East found their way into Europe principally after contact with the Arabs during the Crusades.
Fragrance Raw Materials -
The emphasis on the preservation of wildlife and endangered species in recent years has caused some countries to ban the use of certain animal products. In the United States, the use of ambergris was banned some years ago. More than 96% was a by-product of the whaling industry. Both political considerations and conservation have created many uncertainties as to future supplies of essential oils. For conservation reasons, some countries have blocked further exports of certain materials, and others have begun to regulate export prices. These factors have helped create the uncertainties that abound in natural products and serve to motivate the development of synthetic replacements. In many ways, synthetic materials have better chemical and olfactory uniformity than natural products, as they are not subject to ever-changing weather conditions and natural phenomena. Nevertheless, the use of natural products to achieve certain richness and natural character in perfumes is of paramount importance.
Larousse Gastronomique -
Ambre gris - An intestinal concretion of the sperm-whale. It is found floating on the surface of the seas in the Far East, in the form of wax-like substances, dotted with yellow and black spots, and possessing a strong and pleasant smell. Used in ancient pharmacopoeia as an anitspasmodic, it was also credited with aphrodisiac and restorative properties. Brillat-Savarin [Jean Anthelme Brillat-Savarin, French politician, author and gastronome, 1755-1826] in a positively ecstatic outpouring, sings praises of the restorative powers of chocolat ambré. This product, which was formerly used in confectionery and cookery, is today used in perfumery as a fixative.
The McGraw Hill Encyclopedia of Science and Technology -
It is not known whether the production of ambergris in the gut of the cachalot or sperm whale, Physeter catodon L., is a normal or pathological process. It is always found in association with the sharp beaks of squid, the principal food of the whale, and may be produced simply as a means of protection against damage caused by them. It is found washed up on the shores of China, Japan, Africa, the Americas, tropical islands and in the Bahamas. It has a pleasant, sweet, earthy aroma and is used as a tincture in the fixation of principally floral scents in expensive perfumes. It's use has been almost entirely supplanted by artificial substitutes.
The Merck Index -
A concretion from intestinal tract of the sperm whale, Physeter catodon L., Physeteridae. Found in tropical seas or seashores. It is a gray to black, waxy mass; characteristic odor. d 0. 8-0.92. mp about 60 degrees; flammable; almost completely volatile by heat. Insoluble in water or in alkali hydroxides; sol in hot alcohol, chloroform, ether, fats, volatile oils. Perfumers have used ambergris for centuries for its desirable odoriferous and fixative properties. Three major components isolated are the triterpene alcohol ambrein, epicoprostanol and coprostanone.
Ambergris falls under the Marine Mammal Protection Act of 1972 and is illegal to import in the U.S.A.
Registry of Toxic Effects of Chemical Substances -
RTECS Number: BD8650000 Substance Name: AMBERGRIS TINCTURE CAS Registry Number: 9000-02-6; 1397-88-2 Synonyms: AMBER ; AMBRA ; GRAY AMBER Compound Class: Natural Product; Primary Irritant IRRITATION DATA: Skin Rabbit - 500 mg/24 hrs. Mild FCTXAV 14,675,76 IRRITATION EFFECTS JOURNAL REFERENCES: FCTXAV Food and Cosmetics Toxicology. London, UK V.1-19, 1963-81. For publisher information, see FCTOD7. DATA PRESENT: Irritation Effects