Scientific Periodicals -
- "Ambergris tincture," Food and Cosmetics Toxicology 14(Dec Suppl.):675, 1976
- Not reviewed.
- Barrero A.F. et al.., "Synthesis of Ambrox (R) from communic acids,"
- Tetrahedron 49(28):6251-6262, 1993
- Two routes for preparing Ambrox from the methyl esters of
trans-communic acid and/or cis-communic acid, via selective
degradation of their side chains, stereoselective formation of
the tetrahydrofurane ring, and reduction of the axial methoxycarbonyl
group, are described.
- Barrero A.F. et al., "Amber-type odorants from communic acids,"
- Tetrahedron 49(42):9525-9534, 1993
- A mixture of the methyl esters of communic acids was used in the
synthesis of the ambergris-type odorants Ambrox and ambracetal. Both
syntheses involve methyl ketone as the key intermediate.
- Barrero A.F. et al., "Synthesis of ambrox (R) from (-)-sclareol and
- (+)-cis-abienol," Tetrahedron 49(45):10405-10412, 1993.
- Short and efficient syntheses of (-)-Ambrox (R) (12) from
(-)-sclareol (1) and (+)-cis-abienol (11) are described. In contrast to
previously described procedures, the transformation of 1 to 12, involving
in the key step, an oxidative degradation by catalytic osmium tetroxide,
in the presence of sodium periodate, has the advantage of using the more
suitable sodium borohydride, as the reducing agent. The isolation and
characterization of some reaction intermediates allowed us to confirm
the degradation mechanism.
- Bersuker, I.B. et al., "Structural and electronic origin of ambergris
- odor of cyclic compounds", Nouveau Journal de Chimie
- 9(March 1985):211-18.
- The correlation between structure and ambergris odor of decline
compounds is established using a logical structural analysis employing
stereochemical and electronic structure parameters. A definite structural
fragment (the ambergris triangle) with certain electronic properties
(the acceptor MO) determining the origin of the odor is revealed.
- Bremshey-Wilhelm, M., "Ambergris aroma materials from the sperm-whale,"
- Chemische Rundschau, 40(1941):3
- Ambergris is found in the gut of the sperm whale (potwhale). It is
possible that it represents a pathological product of biotransformation
of isoprenoids found in the whale’s food. Upon extraction of the gray to
black mass with ethanol followed by photooxidation odorless ambrein
yields a strongly ambergris-scented compound, ambrox. Ambrox can be
classified as both a triterpene and a tricyclic, five-ringed ether.
- Brunke, E.-J., "Lower homologues and analogues of ambergris fragrance
- compounds, " in Proceedings of the Seventh International Symposium
- on Olfaction and Taste and of the Fourth Congress of the European
- Chemoreception Research Organization
, ed H. van der Starre,
- London: IRL Press Ltd., 1980, p. 31-14.
- The odor of ambergris tincture is composed of different odor qualities.
A wet earthy and musty odor is combined with sea water, seaweed, tobacco
and fecal notes. An exalting effect of musk type is ascertainable in high
dilutions. The tricyclic ether Ambroxan., which represents the powerful
ambergris effect, has been detected for the first time in the tincture.
As a contribution to the definition of molecular structures that possess
ambergris effect, the author synthesized lower homologues of Ambroxan.
- Büchi, G., and H. Wüest, "The synthesis of racemic Ambrox SUP (R),"
- Helv. Chim. Acta 72 (5) 996-1000, 1989.
- Not reviewed.
- Cambie, R.C. et al., "Chemistry of the Podocarpaceae. [I - LXXV, parts titled
- according to specific subject]," Aust. J. Chem. 20-42:1967-1989.
- A monumental series of over 70 scientific papers by Richard Cambie
and his colleagues at the University of Aukland in New Zealand on the
chemistry of the pandanus family (Podocarpaceae) common in that region
of the world. Many articles published in the period from 1967 to the
present discuss the synthesis of labdanoid and cembranoid compounds
from various terpenes extracted from members of the pandanus family
that have ambergris-like odor characteristics. Cambie and his associates
were among the first to synthetically produce ambergris-like compounds
in commercially feasible quantities.
- Chanslor, J. W., "Treasure from the sea," in Energy from the sea; marine
- resources readings
, ed B. L. Gordon, Watch Hill, RI: The Book and
- Tackle Shop, 1977, p. 318-125.
- Not reviewed.
- Chastrette, M. et al., "On the role of chirality in structure-odor
- relationships," Chem. Senses 17(Oct 1992):555-572.
- Not reviewed.
- Cheetham, P. S. J., "The use of biotransformations for the production
- of flavors and fragrances - flavor, fragrance and cosmetic
- production by biotransformations by fungus, yeast and bacterium,"
- Trends Biotechnol. 11(11):478-88, 1993.
- A review of the literature. The application of novel and commercially
successful processes are discussed including the production of ambergris
aroma chemicals, originally from sperm whales, recently discovered to be
produced by a dimorphic yeast Hyphozyma roseoniger and by Cryptococcus
sp.
- Cortes, M., J. T. Lopez and Y. V. Armstrong, "Synthesis of cyclic acetals
- related to ambergris, " Bol. Soc. Chilena Quim. 37(Dec):279-183, 1992
- Not reviewed.
- Coste-Maniere I.C., J.-P. Zahra and B. Wägell, "Synthesis of ambergris
- fragrance chemicals from sclareol, involving palladium catalysed
- key steps," Tetrahedron Letters 29(9):1017-1020, 1988.
- Not reviewed.
- Decorzant, R., Vial, C. and F. Näf, "A short synthesis of Ambrox from
- sclareol," Tetrahedron 43(8):1871-1879, 1987.
- Not reviewed.
- Dubois, P. A. "Hypotheses relative to the biological origin of ambergris,"
- Parfums, Cosmet., Aromes 19:35-45, 1978.
- Develops the hypothesis that ambergris is produced in the colon of
the sperm whale, Physeter catodon L., in response to irritation caused
by the beaks of ingested squid. The whale secretes a waxy substance,
consisting largely of cholesterol, in response to irritation or damage
which encases the offending objects. Action of the gut microflora
produces changes in color and chemistry in the mass. The concretion
is voided into the sea periodically and undergoes photooxidation in
sea water to become ambergris. In larger whales the concretion may
build up in the colon to pathological levels and even result in death
by intestinal obstruction.
- Farbood, M. I., "Microorganisms as a novel source of flavor compounds -
- flavor and fragrance production," Biochem. Soc. Trans.
- 19(3):690-94, 1991.
- Sclareol conversion to its diol (as a precursor of Ambrox, the
principal scent compound of ambergris) using Hyphozyma roseoniger;
and screening of soil isolates using sclareol as sole C-source to isolate
Cryptococcus albidus ATCC 20918 and ATCC 20921 (sclareolide producer),
Cryptococcus laurentii ATCC 20920 and Bensingtonia ciliata ATCC 20919
(diol producer). These approaches are applicable to the production of
highly-valued natural flavor ingredients. Fermentation processes can be
developed as alternatives to classical organic synthesis for flavor,
fragrance and other fine chemicals.
- Gonzalez-Sierra, M. et al., "A new synthesis of ambrox and related
- compounds," Heterocycles 26(11):2801-1804, 1987.
- Not reviewed.
- Gorbachev, M. Yu. et al., "Role of electronic and structural factors in the
- origin of ambergris-type odors in cyclic compounds", Theoretical and
- Experimental Chemistry
22(May/June 1986):340-4.
- The relationship between the electronic structure and odorant
properties of organic compounds has been investigated. The conclusion
previously drawn in previously regarding the electronic-topological
features characterizing the active portion of the molecule (the
‘ambergris triangle’) has been confirmed on the basis of quantum-chemical
CNDO calculations. Possibilities for designing new compounds with an
ambergris-type odor have been demonstrated with the aid of the prediction
system devised.
- Gore, V. K. et al., "Convenient synthesis of decalin systems of
- bioactive terpenoids," Tetrahedron 49(Mar 26, 1993):2767-1782.
- New analogues of bioactive terpenoids, forskolin, nimbolide,
isozonarol and ambrox have been synthesized using general Diels-Alder
reaction of 2-formyl-4,4-dimethyl-cyclohexa-1,5-dienone with
1,2-disubstituted-1,3-dienes which yielded endo- and exo-adducts.
The deformylation, epimerisation, angular methylation, reduction
and oxidation studies on these adducts have been reported.
- Governo, T. F., R. T. Alessandro and M. J. Prager, "Gas liquid chromatographic
- mass spectrometric detection and identification of ambergris,"
- Journal of the Association of Official Analytical Chemists
- 60(1):160-164, 1977
- A GLC-mass spectrometric method for the detection and identification
of ambergris, a complex mixture of natural compounds produced in the
stomach of the whale, in its natural state or in perfume preparations
is described. Solid samples are extracted; liquid samples are
concentrated. Ambrein, a major component of ambergris, is separated by
GLC on an OV [methyl siloxane polymer]-17 capillary column, detected by
flame ionization, and identified by mass spectrometry. Sample retention
times and mass spectra were compared with those of purified material
isolated from reference ambergris samples. Several types of
perfume-related samples were tested. This method was satisfactory for
samples of high concentration such as ambergris extracts and for
samples of low ambrein concentration typical of perfume formulations.
- Hoffmann, H.-M. and D. Pauluth, "Terpenes and terpenoid compounds. 14.
- Synthesis of oxygenated derivatives in the tetramethyllimonene
- series. New odorants of the wood-ambergris type," Liebigs Ann.
- Chem.
(2):396-402, 1985.
- A practical preparation of tetramethyl-b-terpineol,
cis-tetramethyl-b-terpineol, trans-tetramethyl-b-terpineol,
tetramethyl-(+/-)-8-menthadiene, its spirocyclic epoxide, and
tetramethyl-isocryptone is described. Some of the new
tetramethylated monoterpenes, unlike the simple
C10-monoterpenes, have a woody-ambergris-like odour.
- Hosokawa, H., and T. Shibamoto, "Odor tenacity of perfumery materials,"
- Perfum. Flavor. 2 (7 ):29-10, 1978.
- Not reviewed.
- "Isolating the essentials of fragrance," Manufacturing Chemist 64(Feb):24.
- Ambergris is banned from importation and sale in the U.S. but is still
used elsewhere in the world as a natural ingredient of many fine
fragrances.
- Ivashin, M. V. "Ambra [Ambergris]," Zool. Zhur. 42(7):1099-1103, 1963.
- Ambergris occurs principally in sperm whales greater than 13.5 meters
in length. In freshly killed whales it is found only in the colon where
it is presumed to be formed. Only 3 - 4% of all sperm whales caught in
the Soviet whaling fishery are found to contain ambergris in the gut.
The process of formation may, therefore, be pathological.
- Jegou, Elise, et al., "Ambergris revisited. Isolation of volatile
- constituents; identification and synthesis of ambra-aldehyde C14H22O,"
- Nouv. J. Chim. 1(6):529-11, 1977.
- Not reviewed
- Kawanobe, T., K. Kogami, K. Hayashi and M. Matsui, "New synthesis of
- gamma-homocyclogeranial, gamma-dihydroionone and their derivatives
- (Ambergris)," Agr. Biol. Chem. 48(Feb 1984):461-464.
- Not reviewed
- Lambertsen, R. H. and B. A. Kohn, "Unusual multisystemic pathology in
- a sperm whale bull," J. Wildl. Dis. 23(Jul 1987):510-4.
- This report describes an unusual combination of lesions and apparent
behavioral abnormalities in a sexually mature sperm whale bull taken in
whaling operations off Iceland. Lesions included heavy combative scarring
of the head, grossly roughened and thickened skin on the lower left
flank, cutaneous maculae, genital papillomatosis, partial duodenal
obstruction by plastic debris, colo-rectal obstruction by ambergris,
cystic degeneration of the right kidney, and a deeply ulcerative
gastric nematodiasis. Sealskin was found in the stomach. Gross and
histopathologic observations suggested that the disease complex in
this animal may have been related both to habitat degradation and
health risks naturally associated with its ecology and age.
- Lederer, E., "Sur les constituants de l’ambre gris. I. Isolement d’une
- paraffine liquide," Trav. Membres Bull. Soc. Chim. Biol.
- 25:1239-1241, 1943.
- Ambergris is 4% paraffin liquid C18H38 similar to pristane in fish
oil probably derived from partially digested squid.
- Liu, Shuwen, "Preparation of Ambergris-type perfume from sclareol,"
- Huaxue Shijie 24(4 ):102-5, 1983.
- Not reviewed.
- Lopez J., C. Trespalacios, W. Pena and M. Cortes, "Synthesis of
- g-bicyclohomofarnesal and 14,15,16,20-tetranorlabdan-8b-13-diol,"
- Synth. Commun. 22(17):2599-1605),
- The preparation of the ambergris odorant, g-bicyclohomofarnesal and
14,15,16,20-tetranorlabdan-8b-13-diol from chiral enone is described.
- "The major components of ambergris have been identified as triterpenoid,"
- Perfumer & Flavorist Sep. 1978, p. 54
- Ambergris, a complex mixture of natural compounds which are produced
in the stomach and intestinal tract of the sperm whale, has a bittersweet,
animal odor. Ambrein (ambra-13, 18(28) dien-8-ol), epicoprostanol and
coprostone are the major components of ambergris. TF Governo et al have
described a GC-MS method for determining ambrein and thereby detecting
the use of ambergris concrete in a perfumed preparation, as the presence
of ambrein is proof of the presence of ambergris in a perfume creation.
- Maleczka, R. E., Jr. and L. A. Paquette, "Adaptation of oxyanionic
- sigmatropy to the convergent enantioselective synthesis of
- ambergris-type odorants," Journal of Organic Chemistry,
- 56(23):6538-6546, 1991.
- Not reviewed.
- Martres P. et al., "Synthesis of norambracetal: A new ambergris
- derivative," Tetrahedron Letters 34(19):3127-1128, 1993
- The authors describe the synthesis of norambracetal from sclareol
using gamma-homobicyclo-farnesilic aldehyde as a key intermediate.
- Martres P. et al., "A short and efficient synthesis of (-)-Ambrox
- (R) from (-)-sclareol using a ruthenium oxide catalyzed key
- step," Tetrahedron Letters 34(4):629-632, 1993.
- (-)-Ambrox (R) has been synthesized in 3 steps from natural
(-)-sclareol. Depending on the reoxidizing agents and the reaction
conditions used in the ruthenium oxide catalyzed key step, overall
yields of 79% (NaIO4/RuO4) or 48% (Ca(OCl)2/RuO4-) were observed.
- Mateos A. F. et al., "Synthesis of spiroethers related to ambergris
- fragrances from dimethyl agathate," Bull. Soc. Chim.
- France
, 6(Nov/Dec):898-903, 1991.
- Not reviewed.
- Mookherjee, B. D., and R. R. Patel, "Isolation and identification of
- volatile constituents of tincture ambergris," in Int. Congr.
- Essent. Oils
, (Pap.), 7th, Tokyo, Japan: Japan Flavor
- Fragrance Manufacturer’s Assoc., p. 479-82 , 1979.
- Not reviewed.
- Mori, K. and H. Tamura, "Triterpenoid total synthesis. I. Synthesis
- of ambrein and ambrox," Liebigs Ann. Chem. 1990(4):361-8.
- Not reviewed.
- Nair M.S. and A. T. Anilkumar, "Lipase catalysed regioselective acylation:
- A facile method for the synthesis of commercially important
- ambrox (R) intermediate," Biotechnol. Lett. 6(2):161-162, 1994.
- Not reviewed.
- Nicot, J., "Observations preliminaires sur la mycoflore de l’ambre
- gris, " in Biodegradation et Humification: Rapport du
- Colloque International 1st
: 267-170, 1975.
- Not reviewed.
- Nishi, Y. and H. Ishihara, "Synthesis of (-)-Ambrox (R) from
- (-)-levopimaric acid," Yukagaku 38(4):276-179, 1989.
- Not reviewed.
- Ohloff, G., "The fragrance of ambergris," in Fragrance Chemistry:
- Science of the Sense of Smell
, ed. E. T. Theimer,
- New York: Academic, pp. 535-73, 1982..
- Not reviewed.
- ________, "Stereochemistry-activity relationships in human odor
- sensation: ‘The triaxial rule’" in Proceedings of the
- Seventh International Symposium on Olfaction and Taste and
- of the Fourth Congress of the European Chemoreception Research
- Organization
, ed H. van der Starre, H., London: RL
- Press Ltd., 1980. p. 3-11.
- In several examples the molecular parameters responsible for the
release of ambergris odor are assessed. Stereochemistry supplies the
most essential information. Results obtained from structure modification
are covered by a model which is described in the triaxial rule of odor
sensation. The principle of this molecular rule can be extended to
certain types of natural substances. Thus, sesquiterpene derived from
the eudesmanes and eremophilanes fit very well into the triaxial rule,
as do the odoriferous steroids. In the case of androsta-4,16-dien-1-one,
complete enantioselectivity of odor sensation was found.
- ________ and W. S. Giersch, "Structure-activity relationships in
- odor perception of drimane derivatives," Croat. Chem. Acta
- 58(4):491-509, 1985.
- The woody, ambergris-like odor of trans-decalone derivatives increases
with the introduction of equatorial alkyl substituents in the
C(9)-position and decreases drastically in the corresponding
9-epi derivatives. Complete stereocontrol of odor perception has been
observed. A similar tendency in odor perception has been recognized in
substituted alcohols. The sandalwood-like ambergris note found in
Polywood) disappeared in corresponding alkyl substituted acetates.
The molecular basis of the "steroid-type" scent of some esters was
hitherto unknown.
- ________, K. H. Schulte-Elte and B. L. Müller, "Formation of
- ambergris odorants from ambrein under simulated natural
conditions," Helv. Chim. Acta 60(8):2763-1766, 1977.
- Singlet oxygen oxygenation of ambrein caused degradation of the
primarily formed allyl hydroperoxides to four naturally occurring
ambergris odorants. The results suggest that singlet oxygen is an
active reagent in the biodegradation of the tricyclic triterpene
alcohol ambrein in ambergris, a secretion of the blue sperm whale [sic].
- ________ et al., "Significance of the geminal dimethyl group
- in the odor principle of Ambrox (R)," Helv. Chim. Acta
- 68(7):2022-1029, 1985.
- Not reviewed.
- Opdyke, D. L. J., "Monographs on fragrance raw materials. Ambergris
- tincture," Food Cosmet. Toxicol. 14(Suppl.):675-6, 1976
- Not reviewed.
- Oritani, T., K. Yamashita and M. Matsui, "Chemical studies on ambergris:
- IV. The configuration of ambrein," Agr. Biol. Chem.
- 34(98):1244-1248, 1970.
- The article presents the NMR (nuclear magnetic resonance) spectrum of
ambrein and proposes a chemical stereochemical configuration for the
molecule.
- Ruzicka, L., C. F. Seidell and M. Pfeiffer, "Über die flüchtigen
- Bestandteile des grauen Ambra. 1. Isolierung von
- Dihydro-g-jonon," Helv. Chim. Acta 31(3):827-831, 1948.
- Describes the chemical isolation of dihydro-g-ionone from ambergris.
- Snowden R.L. and S. M. Linder, "A formal synthesis of (+/-)-ambrox (R),"
- Tetrahedron Letters 32(33):4119-4120, 1991.
- Bicyclic diol, a direct precursor of (+/-)-Ambrox (R) ((+/-)-7), has
been synthesized in four steps (35% yield) from the known bicyclic enone.
- Snowden, Roger L. et al., "Internal nucleophilic termination in
- biomimetic acid mediated polyene cyclizations: stereochemical
- and mechanistic implications: synthesis of (+/-)- ambrox and
- its diastereoisomers." Journal of Organic Chemistry
- 57(3)955, Jan 31, 1992.
- The use of excess fluorosulfonic acid in 2- nitropropane allows the
efficient cyclization of isomeric polyenols to norlabdane oxides, which
are tricyclic ethers used as synthetic essences. The triple ring
formation involves the hydroxyl as an internal nucleophilic terminator.
Its stereodirection is determined by the position of the side chain close
to the cyclohexyl, formed either by stereoselective protonation or by
cyclohexyl conformation. The lower rate of isomerization vs. cyclization
ensures that an equatorial side chain yields a trans A/B ring junction
while anaxial chain yields a cis A/B ring junction.
- Snowden, R. L. et al., "Internal nucleophilic termination in
- acid-mediated polyene cyclizations - Synthetic access to
- methyl homologs of (+/-)-Ambrox(R) and its diasteroisomers,"
- Helv. Chim. Acta 76(4):1608-1618, 1993.
- Treatment of ten monocyclic dienols 8-11 with an excess of
fluorosulfonic acid in 2-nitropropane at -90-degrees afforded
diastereoisomeric mixtures of racemic tricyclic ethers 12-14 in 81-91 %
yield (see Tables 1 and 2). These transformations represent further
examples of biomimetic acid-mediated cyclizations in which an OH group
serves as the internal nucleophilic terminator. A non-synchronous process
is postulated, and the examples described strongly re-enforce our working
mechanistic hypothesis, whereby the stereochemical course of cyclizations
is directed by the orientation of the side chain vicinal to the
intermediate cyclohexyl cation (see Schemes 4 and 5). It is also
demonstrated that the efficiency of this process is independent of
the nature of the OH group, which may be primary, secondary, or tertiary.
In addition, the organoleptic properties of 12 14, Me homologs of known
odorants such as Ambrox(R) ((-)-1a) and its diastereoisomers, are briefly
discussed.
- Taha, S. A., "Chemical investigation of the internal secretion of the
- sperm blue whale," Pakhistan Journal of Pharmaceutical
- Sciences
2(2):105-110, 1989.
- Ambergris, which is an internal secretion of the sperm blue whale
[sic], was extracted with 96% ethanol. The saponified and
unsaponified portions were studied in detail. The number of fractions
and components of the unsaponified matter as separated by column and
thin layer chromatography confirm the presence of ambrein (triterpenoid)
as well as some other steroids. The saponified portion is reported to
contain stearic, oleic, linoleic, archidic and betenic acids.
- ________, "Effect of ambrein on blood glucose levels of rats,"
- J. Ethno Pharmacol. 35(2):145-148, 1991.
- The hypoglycemic effect of ambrein, the major constituent of ambergris
from Physeter catodon, on normal and alloxan-diabetic rats is
described. The drug reduced blood glucose in normal and moderately
alloxan-diabetic rats but not in severely diabetic rats. Results suggest
that the hypoglycemic activity may be mediated by enhanced glucose
utilization.
- ________, "Studies on the mode of action of ambrein as a new
- antinociceptive compound," Jap. J. Pharmacol. 60(2):67-72, 1992
- The compound ambrein was isolated from ambergris, which is commonly
used as an analgesic in the Saudi folklore medicine. The LD50 of ambrein,
given intraperitoneally (i.p.) in mice, was found to be high (7.5 g/kg),
and ambrein proved to be a safe compound in this species. In the hot
plate test, ambrein was found to possess antinociceptive activity in
mice at doses which did not sedate or incapacitate the animals. By the
i.p. administration route, ambrein produced antinociception in mice at
a dose as low as 10 mg/kg. The antinociceptive activity of ambrein
(250 mg/kg i.p.) was inhibited by a noradrenergic neurotoxin (DSP-4)
and by naloxone, methysergide or prazosin. It was not influenced by a
serotonin depletor, p-chlorophenylalanine. The possible mechanism of
ambrein antinociception is discussed.
- ________, "The role of prostaglandin E2 in the anti-inflammatory
- and antinociceptive activities of ambrein," Med. Sci.
- Res.
22(Feb 1, 1994):97-98.
- Not reviewed.
- ________ and O. T. Ginawi, "Ambrein, the major constituent of
- ambergris inhibits edema responses to carrageenin and
- serotonin in the rat paw," Bull. Fac. Pharm.
- 31(1):113-15, 1993.
- Ambrein, the major constituent of ambergris, reduced paw edema in
rats induced by carrageenin or serotonin (5-HT), when, it was injected
i.p. at 250 mg/kg/. This effect of ambrein was compared with some known
antiinflammatory drugs such as hydrocortisone, acetyl-salicylic acid
(aspirin) and indomethacin (doses were 40, 350 and 100 mg/kg, i.p. resp.).
The results of this study proved, that ambrein possesses an
antiinflammatory activity, which was less potent than that induced by the
above antiinflammatory drugs in the carrageenin-induced edema, but was
more potent or, at least, equal in potency, in the 5-HT-induced edema
than those caused by the above antiinflammatory drugs. It is concluded
that the antiinflammatory activity of ambrein may be due to inhibition
of systemically released 5-HT and/or prostaglandins.
- Tixier, R., "Sur quelques pigments tetrapyrroliques provenant d’animaux
- marins," Mem. Mus. Nat. Hist. Nat. Ser. A Zool. 5(2):41-132.
- Porphyrins were studied in ambergris. Ambroporphyrin reported earlier
by Y. Okonara is really a mixture of protoporphyrin IX and mesoporphyrin
IX. The beaks of squids damage the sperm whale gut which bleeds. Bacteria
in the gut transform whale hemoglobin from the blood into these
characteristic pigments of ambergris.
- Urones J.G. et al., "Chemistry of labdanediol from Cistus
- ladaniferus
L. synthesis of 12-nor-ambreinolide
- and alpha and beta-levantenolides," Tetrahedron
- 48(47):10389-10398 , 1992.
- Labdanediol, the major component of the neutral part of Cistus
ladaniferus L., was transformed into 12-nor-ambreinolide, precursor
of ambrox (R), in three steps with an overall yield of 70%. Molecular
modeling techniques have been used to determine the stereochemistry of
the by-products of these reactions. The selenylation and elimination
reactions of 2a and beta levantanolides, 2, were used to synthesize
alpha and beta-levantenolides.
- Urones J.G. et al., "Ambergris compounds from labdanolic acid,"
- Tetrahedron 48(45):91-9998), 1992.
- Labdanolic acid (Cistus ladaniferus) is transformed into
derivatives with amber odor. The strategy used allowed a process in which
the oxidative decarboxylation reaction was carried out with the hydroxyl
group protected in ambergris-type woody odorants possessing a
hydronaphthalene skeleton.
- Weyerstahl, P., "Odor and structure.:" Journal für Praktische
- Chemie Chemiker-Zeitung
336 (2):95-109, 1994
- The relationship between molecular structure and aroma properties of
odorants is reviewed with reference to: odour recognition by the olfactory
system; changes in odour occurring with changes in structure; and
structure-odour relationships of classes of odorants of interest to the
fragrance and flavor industries (fatty aldehydes and related compounds,
degraded carotenoids, O-heterocycles, patchouli, sandalwood, ambergris
and steroids, musk).
- Winter, Beatrice, "QSAR in olfaction: ambergris-type odorants," Prog.
- Clin. Biol. Res.
291:401-5, 1989.
- Not reviewed.
- ________, "Ring-opened analogues of Ambrox SUP (R):
- Synthesis and structure-odour relationships," Helv.
- Chim. Acta
72(6):1278-1283, 1989.
- Not reviewed.
- ________, "Studies related to Ambergris-type odorants,"
- Pure Appl. Chem. 62(7):1377-80, 1990
- Not reviewed.
|
