Editing Ambergris

{{Short description|Substance produced in the digestive system of sperm whales}}
{{other uses}}
[[File:Ambergris, Skagway Museum.JPG|thumb|upright=1.3|Ambergris in dried form]]

'''Ambergris''' ({{IPAc-en|ˈ|æ|m|b|ər|g|r|iː|s|}} or {{IPAc-en|ˈ|æ|m|b|ər|g|r|ɪ|s|}}; {{langx|la|ambra grisea}}; {{langx|fro|ambre gris}}), '''''ambergrease''''', or '''grey amber''' is a solid, waxy, flammable substance of a dull grey or blackish colour produced in the digestive system of [[sperm whale]]s.<ref>{{cite encyclopedia |url=https://www.britannica.com/EBchecked/topic/18871/ambergris |title=Ambergris |encyclopedia=Britannica |access-date=31 January 2013 }}</ref> Freshly produced ambergris has a marine, [[feces|fecal]] odor. It acquires a sweet, earthy scent as it ages, commonly likened to the fragrance of [[isopropyl alcohol]] without the vaporous chemical [[astringency]].<ref name="Burr">{{cite book|author=Burr, Chandler|title=The Emperor of Scent: A Story of Perfume, Obsession, and the Last Mystery of the Senses|year=2003|location=New York|publisher=Random House|isbn=978-0-375-50797-7|url=https://archive.org/details/emperorofscentst00burr }}</ref>

Ambergris has been highly valued by [[Perfumer|perfume makers]] as a [[Fixative (perfumery)|fixative]] that allows the scent to last much longer, although it has been mostly replaced by synthetic [[ambroxide]].<ref>Panten, J. and Surburg, H. 2016. Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds. Ullmann's Encyclopedia of Industrial Chemistry. 1–45.</ref> It is sometimes used in cooking.

Dogs are attracted to the smell of ambergris and are sometimes used by ambergris searchers.<ref>{{cite web|url=http://www.ikonlondonmagazine.com/jovoy-paris-designed-for-fascinating-olfactory-experiences/ |title=Jovoy Paris 'Designed' for Fascinating Olfactory Experiences |website=Ikon London Magazine|date=October 2017 |access-date=October 12, 2017}}</ref>

==Etymology==
The English word ''amber'' derives from [[Middle Persian]] [[wiktionary:ʾmbl#Middle_Persian|ʾmbl]], traveling via [[Arabic]] {{lang|ar-Latn|ʿanbar}} ({{lang|ar|[[wikt:عنبر|عنبر]]|rtl=yes}}), <ref name="Amber Etymonline">{{Cite web |title=amber {{!}} Etymology, origin and meaning of amber by etymonline |url=https://www.etymonline.com/word/amber |access-date=2023-01-11 |website=Online Etymology Dictionary}}</ref><ref>Edward Lipinski | Semitic Languages Outline of A Comparative Grammar | Department Of Oriental Studies Leuven Belgium | Assimilation stages of the word Anbar P.189 https://hcommons.org/?get_group_doc=1004138/1673969011-Lipinski_-_Semitic_Languages._Outline_of_a_Comparative_Grammar.pdf</ref> [[Medieval Latin|Middle Latin]] ''ambar,'' and [[Middle French]] ''ambre'' to be adopted in [[Middle English]] in the 14th century.<ref name="Amber Etymonline" />

The word "ambergris" comes from the [[Old French]] ''ambre gris'' or "grey [[amber]]".<ref name="EB1911">{{Cite EB1911 |wstitle=Ambergris |volume=1 |page=794}}</ref><ref>{{cite journal |last=Wedgwood |first=Hensleigh |author-link=Hensleigh Wedgwood |title=On False Etymologies |journal=Transactions of the Philological Society |url=https://babel.hathitrust.org/cgi/pt?id=uc1.b3924121;view=1up;seq=76 |year=1855 |issue=6 |pages=66}}</ref> The addition of "grey" came about when, in the [[Romance languages]], the sense of the word "amber" was extended to [[Baltic amber]] (fossil resin), as white or yellow amber (''ambre jaune''), from as early as the late 13th century.<ref name="Amber Etymonline" /> This fossilized resin subsequently became the dominant (and now exclusive) sense of "amber", leaving "ambergris" as the word for the whale secretion.

The archaic alternate spelling "ambergrease" arose as an [[eggcorn]] from the phonetic pronunciation of "ambergris," encouraged by the substance's waxy texture.<ref name="OED">{{Cite OED|ambergris|access-date=28 February 2023|date=December 2022}}</ref>

==Formation==
Ambergris is formed from a secretion of the [[biliary|bile duct]] in the [[intestines]] of the sperm whale, and can be found floating on the sea or washed up on coastlines. It is sometimes found in the [[abdomen]]s of dead [[sperm whales]].<ref name="EB1911"/> Because the beaks of [[giant squid]]s have been discovered within lumps of ambergris, scientists have hypothesized that the substance is produced by the whale's gastrointestinal tract to ease the passage of hard, sharp objects that it may have eaten.{{Citation needed|date=January 2025}}

Ambergris is passed like fecal matter. It is speculated that an ambergris mass too large to be passed through the intestines is expelled via the mouth, but this remains under debate.<ref>{{cite book |author1=William F. Perrin |author2=Bernd Wursig |author3=J. G.M. [[Hans Thewissen|Thewissen]]|title=Encyclopedia of Marine Mammals |year=2009 |publisher=Academic Press |isbn=978-0080919935 |page=28 }}</ref> Another theory states that an ambergris mass is formed when the colon of a whale is enlarged by a blockage from intestinal worms and [[cephalopod]] parts resulting in the death of the whale and the mass being excreted into the sea.<ref>{{Cite journal |last=Clarke |first=R. |date=2006 |title=The origin of ambergris |url=https://www.lajamjournal.org/index.php/lajam/article/view/231 |journal=Latin American Journal of Aquatic Mammals |volume=5 |pages=7–21 |doi=10.5597/lajam00087 |issn=2236-1057|doi-access=free }}</ref> Ambergris takes years to form. Christopher Kemp, the author of ''Floating Gold: A Natural (and Unnatural) History of Ambergris'', says that it is only produced by sperm whales, and only by an estimated one percent of them. Ambergris is rare; once expelled by a whale, it often floats for years before making landfall.<ref>{{cite book |last=Kemp |first=Christopher |title=Floating Gold: A Natural (and Unnatural) History of Ambergris |url=https://books.google.com/books?id=F0CKIxwLT-oC |year=2012 |publisher=University of Chicago Press |isbn=978-0-226-43036-2 |pages=[https://books.google.com/books?id=F0CKIxwLT-oC&pg=PA12 12–13]}}</ref> The slim chances of finding ambergris and the legal ambiguity involved led perfume makers away from ambergris, and led chemists on a quest to find viable alternatives.<ref name="Daley 2016">{{cite web |last=Daley |first=Jason |title=Your High-End Perfume Is Likely Part Whale Mucus |website=Smithsonian |date=14 April 2016 |url=https://www.smithsonianmag.com/smart-news/your-high-end-perfume-likely-part-whale-mucus-180958767/ |access-date=6 August 2018}}</ref>

Ambergris is found primarily in the [[Atlantic Ocean]] and on the coasts of [[South Africa]]; [[Brazil]]; [[Madagascar]]; the [[East Indies]]; [[The Maldives]]; [[China]]; [[Japan]]; [[India]]; [[Australia]]; [[New Zealand]]; and the [[Maluku Islands|Molucca Islands]]. Most commercially collected ambergris comes from [[the Bahamas]] in the Atlantic, particularly [[New Providence]]. In 2021, fishermen found a 127 kg (280-pound) piece of ambergris off the coast of [[Yemen]], valued at US$1.5 million.<ref>{{cite web|title=A group of fishermen netted a $1.5 million whale-vomit windfall after dredging up a 127 280-pound hunk of the stuff |url=https://www.insider.com/whale-vomit-worth-millions-fishermen-2021-6 |website=Business Insider}}</ref> Fossilised ambergris from 1.75 million years ago has also been found.<ref>{{cite journal |last1=Baldanza |first1=Angela |first2=Roberto |last2=Bizzarri |first3=Federico |last3=Famiani |first4=Paolo |last4=Monaco |first5=Roberto |last5=Pellegrino |first6=Paola |last6=Sassi |title=Enigmatic, biogenically induced structures in Pleistocene marine deposits: A first record of fossil ambergris |journal=Geology |volume=41 |issue=10 |pages=1075 |date=30 July 2013 |doi=10.1130/G34731.1 
|url=https://www.researchgate.net/publication/254559304 |bibcode=2013Geo....41.1075B}}</ref>

==Physical properties==
Ambergris is found in lumps of various shapes and sizes, usually weighing from {{convert|15|g|oz|frac=2|abbr=off}} to {{convert|50|kg|lb|abbr=off}} or more.<ref name="EB1911"/> When initially expelled by or removed from the whale, the fatty precursor of ambergris is pale white in color (sometimes streaked with black), soft, with a strong fecal smell. Following months to years of [[photodegradation]] and [[oxidation]] in the ocean, this precursor gradually hardens, developing a dark grey or black color, a crusty and waxy texture, and a peculiar odor that is at once sweet, earthy, marine, and animalic. Its scent has been generally described as a vastly richer and smoother version of [[isopropanol]] without its stinging harshness. In this developed condition, ambergris has a [[specific gravity]] ranging from 0.780 to 0.926 (meaning it floats in water). It melts at about {{convert|62|C}} to a fatty, yellow resinous liquid; and at {{convert|100|C|0|abbr=on}} it is volatilised into a white vapor. It is soluble in [[diethyl ether|ether]], and in volatile and fixed oils.<ref name="EB1911"/>

==Chemical properties==
Ambergris is relatively nonreactive to acid. White crystals of a [[terpenoid]] known as [[ambrein]], discovered by [[Leopold Ružička]] and Fernand Lardon in 1946,<ref name=ruzicka46>{{cite journal |doi=10.1002/hlca.19460290414|title=Zur Kenntnis der Triterpene. (105. Mitteilung) Über das Ambreïn, einen Bestandteil des grauen Ambra |year=1946 |last1=Ruzicka |first1=L. |last2=Lardon |first2=F. |journal=Helvetica Chimica Acta |volume=29 |issue=4 |pages=912–921}}</ref><ref name="frs">{{cite journal |last1=Prelog |first1=Vladimir |author-link1=Vladimir Prelog |last2=Jeger |first2=Oskar |doi=10.1098/rsbm.1980.0013 |title=Leopold Ruzicka (13 September 1887 &ndash; 26 September 1976) |journal=[[Biogr. Mem. Fellows R. Soc.]] |volume=26 |pages=411–501 |year=1980 |s2cid=71933568 |doi-access=free}}</ref><ref name="hillier19">{{cite journal |last1=Hillier |first1=Stephen G. |last2=Lathe |first2=Richard |title=Terpenes, hormones and life: Isoprene rule revisited |year=2019 |journal=Journal of Endocrinology |volume=242 |issue=2 |pages=R9–R22 |pmid=31051473 |doi=10.1530/JOE-19-0084 |doi-access=free}}</ref> can be separated from ambergris by heating raw ambergris in alcohol, then allowing the resulting solution to cool. Breakdown of the relatively scentless ambrein through oxidation produces [[ambroxide]] and ambrinol, the main odor components of ambergris.

<gallery widths="150" heights="200">
File:Ambrein.svg|Ambrein
File:Ambrox.svg|Ambroxide
File:Ambrinol.svg|Ambrinol
</gallery>

[[Ambroxide]] is now produced synthetically and used extensively in the perfume industry.<ref>{{cite web |url=http://perfumeshrine.blogspot.co.uk/2010/11/ambroxambroxan-modern-fascination-on.html |title=Ambrox/Ambroxan: a Modern Fascination on an Elegant Material |date=5 November 2010 |publisher=Perfume Shrine |access-date=31 January 2013 }}</ref>

==Applications==
Ambergris has been mostly known for its use in creating perfume and fragrance much like [[musk]]. Perfumes based on ambergris still exist.<ref>{{cite magazine |url=http://www.businessweek.com/magazine/ambergris-treasure-of-the-deep-01122012.html |archive-url=https://web.archive.org/web/20120114153426/http://www.businessweek.com/magazine/ambergris-treasure-of-the-deep-01122012.html |url-status=dead |archive-date=January 14, 2012 |title=Ambergris, Treasure of the Deep |date=January 12, 2012 |first=Eric |last=Spitznagel |magazine=Bloomberg Businessweek |access-date=31 January 2013 }}</ref>
Ambergris has historically been used in food and drink. A serving of eggs and ambergris was reportedly King [[Charles II of England]]'s favorite dish.<ref>{{cite book |author=Lord Macaulay |title=The History of England from the Accession of James II |year=1848 |publisher=Harper |chapter-url=http://www.gutenberg.org/ebooks/1468 |volume=1 |chapter=IV |page=222 |author-link=Thomas Babington Macaulay, 1st Baron Macaulay }}</ref> A recipe for [[Shrub (drink)|Rum Shrub]] liqueur from the mid 19th century called for a thread of ambergris to be added to rum, almonds, cloves, cassia, and the peel of oranges in making a cocktail from ''[[The English and Australian Cookery Book]]''.<ref>{{cite book |last=Abbott |first=Edward |url=https://archive.org/details/b21505524 |title=The English and Australian Cookery Book |date=1864 |page=[https://archive.org/details/b21505524/page/272 272] (at the top)}}</ref> It has been used as a flavoring agent in Turkish coffee<ref>{{cite web |url=http://www.theguideistanbul.com/istanbul-historic-coffeehouses/ |title=The starting point of Turkish coffee: Istanbul's historic coffeehouses |website=The Istanbul Guide |access-date=26 October 2018 |archive-date=18 October 2020 |archive-url=https://web.archive.org/web/20201018170334/https://www.theguideistanbul.com/istanbul-historic-coffeehouses/ |url-status=dead }}</ref> and in hot chocolate in 18th century Europe.<ref name="Green">{{cite news|last1=Green|first1=Matthew|title=How the decadence and depravity of London's 18th century elite was fuelled by hot chocolate|url=https://www.telegraph.co.uk/travel/destinations/europe/united-kingdom/england/london/articles/surprising-history-of-london-chocolate-houses/ |archive-url=https://ghostarchive.org/archive/20220112/https://www.telegraph.co.uk/travel/destinations/europe/united-kingdom/england/london/articles/surprising-history-of-london-chocolate-houses/ |archive-date=2022-01-12 |url-access=subscription |url-status=live|work=The Daily Telegraph|access-date=July 15, 2017|date=March 11, 2017}}{{cbignore}}</ref> The substance is considered an [[aphrodisiac]] in some cultures.<ref name="uchicago1">{{cite book |last=Kemp |first=Christopher |url=https://books.google.com/books?id=akaxh794PdAC |title=Floating Gold: A Natural (& Unnatural) History of Ambergris |chapter-url=http://press.uchicago.edu/books/excerpt/2012/kemp_floating.html |chapter=The Origin of Ambergris |date=2012-05-11 |oclc=787843317|isbn=9780226430379 |publisher=University of Chicago Press}}</ref>

[[Ancient Egypt]]ians burned ambergris as incense, while in modern [[Egypt]] ambergris is used for scenting cigarettes.<ref name="MatHB">{{cite book |chapter=Ambergris |title=Materials Handbook: An Encyclopedia for Managers, Technical Professionals, Purchasing and Production Managers, Technicians, and Supervisors |page=64 |last1=Brady |first1=George Stuart |last2=Clauser |first2=Henry R. |last3=Vaccari |first3=John A. |isbn=978-0-07-136076-0 |year=2002 |publisher=McGraw-Hill}}</ref> {{anchor|Chinese }}The [[History of China#Ancient China|ancient Chinese]] called the substance "dragon's spittle fragrance".<ref name=sciam>{{cite magazine |url=http://www.scientificamerican.com/article.cfm?id=strange-but-true-whale-waste-is-valuable |title=Strange but True: Whale Waste Is Extremely Valuable |date=April 26, 2007 |first=Cynthia |last=Graber |magazine=Scientific American |access-date=31 January 2013}}</ref> During the [[Black Death]] in [[Europe]], people believed that carrying a ball of ambergris could help prevent them from contracting plague. This was because the fragrance covered the smell of the air which was believed to be a [[Miasma theory of disease|cause of plague]].

During the [[Middle Ages]], Europeans used ambergris as a [[Pharmaceutical drug|medication]] for [[headache]]s, [[Common cold|colds]], [[epilepsy]], and other ailments.<ref name=sciam />

==Legality==
{{Main|International Whaling Commission#1982 moratorium}}
From the 18th to the mid-19th century, the whaling industry prospered. By some reports, nearly 50,000 whales, including sperm whales, were killed each year. Throughout the 19th century, "millions of whales were killed for their oil, whalebone, and ambergris" to fuel profits, and they soon became endangered as a species as a result.<ref>{{Cite book|title=For Appearance' Sake: The Historical Encyclopedia of Good Looks, Beauty, and Grooming|last=Sherrow|first=Victoria L.|publisher=Greenwood|year=2001|isbn=9781573562041|pages=[https://archive.org/details/forappearancesak00sher/page/129 129]|url=https://archive.org/details/forappearancesak00sher/page/129}}</ref> Due to studies showing that the whale populations were being threatened, the International Whaling Commission instituted a [[Moratorium (law)|moratorium]] on commercial whaling in 1982. Although ambergris is not harvested from whales, many countries also ban the trade of ambergris as part of the more general ban on the hunting and exploitation of whales.

Urine, faeces, and ambergris (that has been naturally excreted by a sperm whale) are waste products not considered parts or derivatives of a [[CITES]] species and are therefore not covered by the provisions of the convention.<ref>[https://cites.org/sites/default/files/common/cop/16/sum/E-CoP16-Com-II-Rec-02.pdf CITES CoP16 Com. II Rec. 2 (Rev. 1), Convention on International Trade in Endangered Species of Wild Fauna and Flora, Sixteenth meeting of the Conference of the Parties Bangkok (Thailand), 3–14 March 2013 Summary record of the second session of Committee II]</ref>

Countries where ambergris trade is illegal include:
* Australia – Under federal law, the export and import of ambergris for commercial purposes is banned by the [[Environment Protection and Biodiversity Conservation Act 1999]]. The various states and territories have additional laws regarding ambergris.<ref>{{cite web|url=http://www.environment.gov.au/coasts/species/cetaceans/education/ambergris.html |title=Whale and Dolphin permits – Ambergris |publisher=Environment.gov.au |date=1979-06-28 |access-date=2014-03-13}}</ref>
* United States – The possession and trade of ambergris is prohibited by the [[Endangered Species Act of 1973]].<ref>{{cite magazine|url=http://www.businessweek.com/magazine/ambergris-treasure-of-the-deep-01122012.html#p2 |archive-url=https://web.archive.org/web/20120114153426/http://www.businessweek.com/magazine/ambergris-treasure-of-the-deep-01122012.html#p2 |url-status=dead |archive-date=January 14, 2012 |title=Ambergris, Treasure of the Deep |magazine=Businessweek |date=2012-01-12 |access-date=2014-03-13}}</ref>
* India – Sale or possession is illegal under the [[Wild Life (Protection) Act, 1972]].

Countries where trade of ambergris is legal include:
* United Kingdom<ref name=":0">{{cite web|title=Ambergris: lucky, lucrative and legal?|date=10 September 2015|url=http://us.whales.org/blog/2015/09/ambergris-lucky-lucrative-and-legal}}</ref>
* France<ref name=":0" />
* Switzerland<ref name=":0" />
* Maldives<ref name=":0" />

==References==
{{Reflist|30em}}

==Further reading==
* {{cite journal |last1=Borschberg |first1=Peter |title=''O comércio de âmbar asiático no início da época moderna (séculos XV–XVIII)'' |trans-title=The Asiatic Ambergris trade in the early modern period (15th to 18th century) |language=pt |editor1-first=Carla Alferes |editor1-last=Pinto |journal=Oriente |location=Lisbon |publisher=Fundação Oriente |volume=8 |date=April 2004 |pages=3–25}} [http://montalvoeascinciasdonossotempo.blogspot.sg/2011/10/peter-borschberg-o-comercio-de-ambar.html montalvoeascinciasdonossotempo.blogspot], accessed 21 August 2015
* {{cite journal |doi=10.5597/lajam00087 |url=http://lajamjournal.org/index.php/lajam/article/viewFile/231/183 |title=The origin of ambergris |year=2006 |last1=Clarke |first1=Robert |journal=Latin American Journal of Aquatic Mammals |volume=5 |issue=1 |pages=7–21|doi-access=free }}
* {{cite journal |first1=Karl H. |last1=Dannenfeldt |url=http://paydirt-discourse.s3-us-west-2.amazonaws.com/original/2X/b/bcb672ced09f409be638a4e41795dd33eaf94173.pdf |archive-url=https://web.archive.org/web/20191024145026/http://paydirt-discourse.s3-us-west-2.amazonaws.com/original/2X/b/bcb672ced09f409be638a4e41795dd33eaf94173.pdf |url-status=dead |archive-date=2019-10-24 |title=Ambergris: The Search for Its Origin |journal=Isis |pmid=6757176 |jstor=231442 |year=1982 |volume=73 |issue=268 |pages=382–97 |doi=10.1086/353040|s2cid=30323379 }}
* {{cite journal |doi=10.1098/rstl.1724.0053 |title=An Essay upon the Natural History of Whales, with a Particular Account of the Ambergris Found in the Sperma Ceti Whale. In a Letter to the Publisher, from the Honourable Paul Dudley, Esq; F. R. S |year=1724 |last1=Dudley |first1=Paul |journal=Philosophical Transactions of the Royal Society |volume=33 |issue=381–91 |pages=256–69 |jstor=103782 |bibcode=1724RSPT...33..256D|s2cid=186208376 }}
* {{cite book |last=Kemp |first=Christopher |title=Floating Gold: A Natural (and Unnatural) History of Ambergris |url=https://books.google.com/books?id=F0CKIxwLT-oC |date=2012|publisher=University of Chicago Press |isbn=978-0-226-43036-2}}
* {{cite book |first1=Christopher |last1=Kemp |year=2012 |chapter=The Origin of Ambergris |chapter-url=http://www.press.uchicago.edu/books/excerpt/2012/kemp_floating.html |title=Floating Gold: A Natural (and Unnatural) History of Ambergris |location=Chicago |publisher=University of Chicago Press |pages=8–16 |isbn=978-0-226-43036-2}}
* {{cite journal |doi=10.1021/ci034203t |pmid=15032539 |url=http://members.cbio.mines-paristech.fr/~jvert/svn/bibli/local/Kovatcheva2004Combinatorial.pdf |archive-url=https://web.archive.org/web/20180722183611/http://members.cbio.mines-paristech.fr/~jvert/svn/bibli/local/Kovatcheva2004Combinatorial.pdf |url-status=dead |archive-date=2018-07-22 |title=Combinatorial QSAR of Ambergris Fragrance Compounds |year=2004 |last1=Kovatcheva |first1=Assia |last2=Golbraikh |first2=Alexander |last3=Oloff |first3=Scott |last4=Xiao |first4=Yun-De |last5=Zheng |first5=Weifan |last6=Wolschann |first6=Peter |last7=Buchbauer |first7=Gerhard |last8=Tropsha |first8=Alexander |journal=Journal of Chemical Information and Modeling |volume=44 |issue=2 |pages=582–95|citeseerx=10.1.1.411.7708 }}
* {{cite journal |doi=10.1002/hlca.19800630721 |title=Stereochemistry-Odor Relationships in Enantiomeric Ambergris Fragrances |year=1980 |last1=Ohloff |first1=Günther |last2=Vial |first2=Christian |last3=Wolf |first3=Hans Richard |last4=Job |first4=Kurt |last5=Jégou |first5=Elise |last6=Polonsky |first6=Judith |last7=Lederer |first7=Edgar |journal=Helvetica Chimica Acta |volume=63 |issue=7 |pages=1932–46 |citeseerx=10.1.1.880.1000 }}

==External links==
{{Wiktionary}}
* [https://www.naturalhistorymag.com/picks-from-the-past/151686/floating-gold Natural History Magazine Article (from 1933): Floating Gold – The Romance of Ambergris]
* [https://web.archive.org/web/20060201072605/http://netstrider.com/documents/ambergris/ Ambergris – A Pathfinder and Annotated Bibliography]
* [https://web.archive.org/web/20060302082728/http://www.cropwatch.org/amber.htm On the chemistry and ethics of Ambergris]
* [https://www.theguardian.com/environment/2023/jul/04/las-palmas-pathologist-ambergris-block-dead-sperm-whale Pathologist finds €500,000 ‘floating gold’ in dead whale in Canary Islands]
{{Whaling}}

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