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39-491: Samuel Enderby (17 January 1719 – 19 September 1797) was an English whale oil merchant, significant in the history of whaling in the United Kingdom . In the 18th century, he founded Samuel Enderby & Sons , a prominent shipping, whaling , and sealing company. The Enderby family had been tanners (leather workers) at Bermondsey , and supported Oliver Cromwell . Daniel Enderby I raised money for

78-549: A broad range of temperatures. Cocoa butter is unusual in that it is composed of only a few triglycerides, derived from palmitic , oleic , and stearic acids in the 1-, 2-, and 3-positions of glycerol, respectively. The simplest triglycerides are those where the three fatty acids are identical. Their names indicate the fatty acid: stearin derived from stearic acid, triolein derived from oleic acid , palmitin derived from palmitic acid , etc. These compounds can be obtained in three crystalline forms ( polymorphs ): α, β, and β′,

117-406: A given number of carbon atoms – that is, it is "saturated" with hydrogen atoms.) Unsaturated fatty acids are further classified into monounsaturated (MUFAs), with a single double bond, and polyunsaturated (PUFAs), with two or more. Natural fats usually contain several different saturated and unsaturated acids, even on the same molecule. For example, in most vegetable oils,

156-572: A lower melting point than saturated analogues; as a result, they are often liquid at room temperature. The three fatty acids substituents can be the same, but they are usually different. Many triglycerides are known because many fatty acids are known. The chain lengths of the fatty acid groups vary in naturally occurring triglycerides, Those containing 16, 18, or 20 carbon atoms are defined as long-chain triglycerides , while medium-chain triglycerides contain shorter fatty acids. Animals synthesize even-numbered fatty acids, but bacteria possess

195-898: A memoir about his years as a captive of the Nuu-chah-nulth (Nootka), an Indigenous Pacific Northwest people on the British Columbia Coast , from 1802 to 1805, claimed whale oil was a condiment with every dish, even strawberries. In Robert Browning's Pied Piper (§ VII), the Piper's piping leads the rats to imagine the sound of "breaking the hoops of train-oil flasks". Friedrich Ratzel in The History of Mankind (1896), when discussing food materials in Oceania , quoted Captain James Cook 's comment in relation to

234-659: A weight basis, 10.75, 10.71, 10.66, and 10.58 kcal/g – a decrease of about 0.6% for each additional double bond. The greater the degree of unsaturation in a fatty acid (i.e., the more double bonds in the fatty acid) the more vulnerable it is to lipid peroxidation ( rancidity ). Antioxidants can protect unsaturated fat from lipid peroxidation. While it is the nutritional aspects of polyunsaturated fatty acids that are generally of greatest interest, these materials also have non-food applications. Linseed oil and related oils are important components of useful products used in oil paints and related coatings. Linseed oil

273-401: Is a solid near room temperature, but most examples are oils. Their density is near 0.-0.9 g/cm . Triglycerides are tri- esters derived from the condensation reaction of glycerol with three fatty acids . Their formation can be summarised by the following overall equation: In nature, the formation of triglycerides is not random; rather, specific fatty acids are selectively condensed with

312-515: Is as precise as the IUPAC one but easier to parse, is a code of the form "{N}:{D} cis -{CCC} trans -{TTT}", where {N} is the number of carbons (including the carboxyl one), {D} is the number of double bonds, {CCC} is a list of the positions of the cis double bonds, and {TTT} is a list of the positions of the trans bonds. Either or both cis and trans lists and their labels are omitted if there are no multiple bonds with that geometry. For example,

351-425: Is clear, and varies in color from a bright honey yellow to a dark brown, according to the condition of the blubber from which it has been extracted and the refinement through which it went. It has a strong fishy odor . When hydrogenated , it turns solid and white and its taste and odor change. Its composition varies with the species from which it was sourced and the method by which it was harvested and processed. It

390-410: Is composed mainly of triglycerides (molecules of fatty acids attached to a glycerol molecule). Oil sourced from toothed whales, especially the oil of sperm whales , contains a substantial amount of wax esters . Most of the fatty acids are unsaturated. The most common fatty acids are oleic acid and its isomers (18:1 carbon chains). Whale oil is exceptionally stable. The main use of whale oil

429-630: Is rich in di- and tri-unsaturated fatty acid components, which tend to harden in the presence of oxygen. This heat-producing hardening process is peculiar to these so-called drying oils . It is caused by a polymerization process that begins with oxygen molecules attacking the carbon backbone. Aside from llinseed oil, other oils exhibit drying properties and are used in more specialized applications. These include tung , poppyseed , perilla , and walnut oil . All " polymerize " on exposure to oxygen to form solid films, useful in paints and varnishes . Triglycerides can also be split into methyl esters of

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468-408: Is sometimes misquoted as saying that whale oil is "as rare as the milk of queens". The quote is: In merchantmen, oil for the sailor is more scarce than the milk of queens. According to the rest of the paragraph, sailors onboard the merchantman had to sleep, dress, and maneuver below decks in the dark as opposed to the whalers who used the oil for light. John R. Jewitt , an Englishman who wrote

507-518: Is still permitted. Groups such as the Inuit of North America are granted special whaling rights, integral to their culture , and they still use whale oil as a food and as lamp oil in the ceremonial qulliq . Whale oil was used as a cheap illuminant, though it gave off a strong odor when burnt and was not very popular. It was replaced in the late 19th century by cheaper, more efficient , and longer-lasting kerosene . Burning fluid and camphine were

546-612: Is used to turn vegetable oils into solid or semisolid vegetable fats like margarine , which can substitute for tallow and butter and (unlike unsaturated fats) resist rancidification . Under some conditions, hydrogenation can creates some unwanted trans acids from cis acids. In cellular metabolism , unsaturated fat molecules yield slightly less energy (i.e., fewer calories ) than an equivalent amount of saturated fat. The heats of combustion of saturated, mono-, di-, and tri-unsaturated 18-carbon fatty acid esters have been measured as 2859, 2828, 2794, and 2750 kcal/mol, respectively; or, on

585-490: The Māori people : "No Greenlander was ever so sharp set upon train-oil as our friends here, they greedily swallowed the stinking droppings when we were boiling down the fat of dog-fish." Triglyceride Many types of triglycerides exist. One specific classification focuses on saturated and unsaturated types. Saturated fats have no C=C groups; unsaturated fats feature one or more C=C groups. Unsaturated fats tend to have

624-405: The 1820s, when piped coal-gas networks began to provide an alternative lighting fuel in urban areas. Due to dwindling whale populations causing higher voyage costs, as well as taxation , the market changed rapidly in the 1860s after the discovery of mineral oils and expansion of chemical refineries to produce kerosene and lubricants . By 1870, kerosene became the dominant illumination fuel and

663-413: The 20th century it was made into margarine . With the commercial development of the petroleum industry and vegetable oils , the use of whale oils declined considerably from its peak in the 19th century into the 20th century. This is said to have saved whales from extinction . In the 21st century, with most countries having banned whaling, the sale and use of whale oil has practically ceased. Whale oil

702-453: The Dutch word traan ("tear drop"). Sperm oil , a special kind of oil obtained from the head cavities of sperm whales , differs chemically from ordinary whale oil: it is composed mostly of liquid wax . Its properties and applications differ from those of regular whale oil, and it was sold for a higher price. Emerging industrial societies used whale oil in oil lamps and to make soap . In

741-419: The ability to synthesise odd- and branched-chain fatty acids. As a result, ruminant animal fat contains odd-numbered fatty acids, such as 15, due to the action of bacteria in the rumen . Many fatty acids are unsaturated; some are polyunsaturated (e.g., those derived from linoleic acid ). Most natural fats contain a complex mixture of individual triglycerides. Because of their heterogeneity, they melt over

780-426: The animal fats tallow and lard are high in saturated fatty acid content and are solids. Olive and linseed oils on the other hand are unsaturated and liquid. Unsaturated fats are prone to oxidation by air, which causes them to become rancid and inedible. The double bonds in unsaturated fats can be converted into single bonds by reaction with hydrogen effected by a catalyst. This process, called hydrogenation ,

819-661: The army in the Long Parliament, as recorded in Hansard. The family was granted forfeited estates at Lismore, County Waterford , Ireland, which were sold in 1660. After that time, the family was active in the 'oil and Russia trade' and traded with the New England colonies. On 2 June 1752, Samuel Enderby II married Mary Buxton, a daughter of his business partner, at St Paul's Wharf in London. Enderby died in 1797, leaving

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858-400: The codes for stearic, oleic, elaidic, and vaccenic acids are "18:0", "18:1 cis -9", "18:1 trans -9", and "18:1 trans -11", respectively. Catalpic acid , (9 E ,11 E ,13 Z )-octadeca-9,11,13-trienoic acid according to IUPAC nomenclature, has the code "18:3 cis -13 trans -9,11". For human nutrition, an important classification of fats is based on the number and position of double bonds in

897-436: The company to his three sons Charles, Samuel III, and George. Samuel Enderby III (1755-1829) owned Britannia , the ship that made the first successful whale catch off Australia (10 November 1791). He was the grandfather of Major-General Charles George Gordon . Whale oil Whale oil is oil obtained from the blubber of whales . Oil from the bowhead whale was sometimes known as train-oil , which comes from

936-400: The constituent fatty acids via transesterification : The resulting fatty acid methyl esters can be used as fuel in diesel engines , hence their name biodiesel . Staining for fatty acids, triglycerides, lipoproteins, and other lipids is done through the use of lysochromes (fat-soluble dyes). These dyes can allow the qualification of a certain fat of interest by staining the material

975-406: The constituent fatty acids. Saturated fat has a predominance of saturated fatty acids , without any double bonds, while unsaturated fat has predominantly unsaturated acids with double bonds. (The names refer to the fact that each double bond means two fewer hydrogen atoms in the chemical formula. Thus, a saturated fatty acid, having no double bonds, has the maximum number of hydrogen atoms for

1014-562: The dominant replacements for whale oil until the arrival of kerosene. In the United States, whale oil was used in cars as a constituent of automatic transmission fluid until it was banned by the Endangered Species Act of 1973 . It was also a major component of hydraulic fluid in tractors (like the ubiquitous JDM Type 303 Special Hydraulic Fluid) until its withdrawal in 1974. In the United Kingdom, whale oil

1053-481: The hydroxyl functional groups of glycerol. Animal fats typically have unsaturated fatty acid residues on carbon atoms 1 and 3. Extreme examples of non-random fats are cocoa butter (mentioned above) and lard , which contains about 20% triglyceride with palmitic acid on carbon 2 and oleic acid on carbons 1 and 3. An early step in the biosynthesis is the formation of the glycerol-1-phosphate : The three oxygen atoms in this phosphate ester are differentiated, setting

1092-605: The name for a brood pheromone of the honey bee. Where the fatty acid residues in a triglyceride are all the same, names like olein (for glyceryl trioleate) and palmitin (for glyceryl tripalmitate) are common. In the International Union of Pure and Applied Chemistry 's (IUPAC's) general chemical nomenclature for organic compounds , any organic structure can be named by starting from its corresponding hydrocarbon and then specifying differences so as to describe its structure completely. For fatty acids, for example,

1131-402: The position and orientation of carbon-carbon double bonds is specified counting from the carboxyl functional group . Thus, oleic acid is formally named (9 Z )-octadec-9-enoic acid, which describes that the compound has: IUPAC nomenclature can also handle branched chains and derivatives where hydrogen atoms are replaced by other chemical groups. Triglycerides take formal IUPAC names according to

1170-420: The rule governing naming of esters. For example, the formal name propane-1,2,3-tryl 1,2-bis((9 Z )-octadec-9-enoate) 3-(hexadecanoate) applies to the pheromone informally named as glyceryl 1,2-dioleate-3-palmitate, and also known by other common names including 1,2-dioleoyl-3-palmitoylglycerol, glycerol dioleate palmitate, and 3-palmito-1,2-diolein. A notation specific for fatty acids with unbranched chain, that

1209-464: The saturated palmitic (C16:0) and stearic (C18:0) acid residues are usually attached to positions 1 and 3 (sn1 and sn3) of the glycerol hub, whereas the middle position (sn2) is usually occupied by an unsaturated one, such as oleic (C18:1, ω–9) or linoleic (C18:2, ω–6). ) Saturated fats generally have a higher melting point than unsaturated ones with the same molecular weight, and thus are more likely to be solid at room temperature. For example,

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1248-688: The stage for regiospecific formation of triglycerides, as the diol reacts selectively with coenzyme-A derivatives of the fatty acids, RC(O)S–CoA: The phosphate ester linkage is then hydrolysed to make way for the introduction of a third fatty acid ester: Fats are often named after their source, e.g., olive oil , cod liver oil , shea butter , tail fat . Some have traditional names of their own, e.g., butter, lard, ghee , and margarine . The composition of these natural fats are somewhat variable. The oleic acid component in olive oil can vary from 64-86%. Triglycerides are then commonly named as esters of those acids, as in glyceryl 1,2-dioleate 3-palmitate,

1287-411: The three forms differing in their melting points. A triglyceride containing different fatty acids is known as a mixed triglyceride . These are more common in nature. If the first and third fatty acids on the glycerol differ, then the mixed triglyceride is chiral . Triglycerides are colorless, although degraded samples can appear yellowish. Stearin, a simple, saturated, symmetrical triglyceride,

1326-475: The water. Baleen whales were a major source of whale oil. Their oil is exclusively composed of triglycerides , whereas that of toothed whales contains wax esters . The bowhead whale and right whale were considered the ideal whaling targets. They are slow and docile, and they float when killed. They yield plenty of high-quality oil and baleen , and as a result, they were hunted nearly to extinction. Whale oil has low viscosity (lower than olive oil ),

1365-511: The whaling industry was in decline. The use of whale oil had a steady decline starting in the late 19th century due to the development of superior alternatives, and later, the passing of environmental laws . In 1986, the International Whaling Commission declared a moratorium on commercial whaling , which has all but eliminated the use of whale oil today. Aboriginal whaling , part of the subsistence economy ,

1404-576: Was for illumination and machine lubrication . Cheaper alternatives to whale oil existed, but were inferior in performance and cleanliness of burn. As a result, whale oil dominated the world for both uses. This in turn further fueled the Industrial Revolution , in the United States , in Britain , and continental Europe . As demand for whale oil increased at the end of the 18th century, the whaling industry expanded until its peak around

1443-405: Was obtained by boiling strips of blubber harvested from whales. The removal is known as flensing and the boiling process was called trying out . The boiling was carried out on land in the case of whales caught close to shore or beached. On longer deep-sea whaling expeditions, the trying-out was done aboard the ship in a furnace known as a trywork and the carcass was then discarded into

1482-496: Was used in toolmaking machinery as a high-quality lubricant. After the invention of hydrogenation in the early 20th century, whale oil was used to make margarine, a practice that has since been discontinued. Whale oil in margarine has been replaced by vegetable oil . Whale oil was used to make soap. Until the invention of hydrogenation, it was used only in industrial-grade cleansers, because its foul smell and tendency to discolor made it unsuitable for cosmetic soap. Whale oil

1521-789: Was widely used in the First World War as a preventive measure against trench foot . An infantry battalion of the British Army during World War I on the Western Front could be expected to use 10 imp gal (45 L; 12 US gal) of whale oil a day. The oil was rubbed directly onto bare feet in order to protect them from the effects of immersion. The pursuit and use of whale oil, along with many other aspects of whaling , are discussed in Herman Melville's 1851 novel, Moby-Dick . The novel's narrator

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