Stillingia oil

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Stillingia oil is an oil extracted (by solvents) from the seeds of plants of the Triadica genus such as Triadica sebifera (Chinese tallow tree) and Triadica cochinchinensis (Mountain tallow tree). [1] [2] [3] It is a drying oil used in paints and varnishes, [4] and it is believed to be toxic in China. [5] It must be distinguished from stillingia tallow, a fatty substance that surrounds the seeds in the fruit and must be removed before extracting the oil. [2] [5]

The name of the oil was given when the two plants were classified in the genus Stillingia , with binomial names "Stillingia sebifera" and "Stillingia discolor". Sometime prior to 1950 the species were reclassified in the genus Sapium , and articles from the 1950s still use the names "Sapium sebiferum" and "Sapium discolor" However, since about 2002 the plants have been reclassified again in the genus Triadica , and the second one had its species name changed to "cochinchinensis". [6]

Stillingia oil has a typical drying time of 4–6 hours. The seeds produce 20-30% w/w of tallow fat and 10-17% w/w of stillingia oil. [5] It has iodine number 127, [7] a saponification value of 206, [7] [8] and a thiocyanogen value of 100.7. [8]

Composition

The composition of the oil may vary considerably with the age of the seeds (which can remain on the tree for a year after maturation) and with the extraction process. [9] The major components of typical fresh oil are triglycerides of the following fatty acids: [2]

Fatty acid(a) %(b) [2]  %(b) [7]
trans-2,cis-4-decadienoic acid (C10:2)D8
lauric acid (C12:0)R3.5
palmitic acid (C16:0)P98
heptadecanoic acid (C17:0)H1.8
stearic acid (C18:0)S42.5
oleic acid (C18:1)O816
linoleic acid (C18:2)L2529
linolenic acid (C18:3)N4540
arachidic acid (C20:0)Atrace

(a) Fatty acid codes used in the discussion below.
(b) Molar percentages.

Several analyses of authentic oil in the 1950s [10] [3] found significant amounts of 2.4-decadienoic acid, later identified as the trans-2, cis-4 isomer, [5] which had not been detected in natural oils before, and was conjectured to play a relatively prominent part in the drying and polymerizing properties of stillingia oil. Another analysis (1992) found that the tocopherol fraction contains nearly pure (92%) γ-tocotrienol. [11]

According to a 1953 analysis of authentic oil, 64% (by mass) of the oil's triglycerides have three unsaturated acyls connected to the glycerol hub, 34% have two, and about 2% have just one. The most common triglyceride component, with over half the mass, had (1) one linoleic and two linolenic acyls, or LNN or NLN using the codes of the table above. The next two most common types have a 2,4-decadienoic acyl on the second carbon of the glycerol hub, flanked by (2) one linoleic and one linolenic acyl (LDN), or (3) two linolenic acyls (NDN). The 2,4-decadienoic acyl occurs almost exclusively in those two components. There are smaller proportions of triglycerides with (4) one saturated, one linoleic, and one linolenic (XLN, LXN, etc.); (5) one saturated and two linolenic; (XNN or NXN) (6) one oleic, one linoleic, one linolenic (OLN, LON, etc.); and (7) one oleic and two linolenic (ONN o NON). [10] Over 95% of the triglycerides in stillingia oil were found to have three doubly-unsaturated fatty acids. This proportion is greater than that of linseed oil, and comparable with that in conophor oil. [10]

An analysis in 1992 found that an 8-hydroxy-5,6-octadienoic acid was joined to by an estolide linkage to the 2,4-decadienoic acyl. [5]

A more recent analysis (2009) of commercial oil found instead 80% (molar) of LLN, 14% PLN, 3% PPL, 1.5 RPL, and 0.5 SLN. [7] This analysis also failed to find the 2,4-decadienoic acid. Instead it found twice as much oleic acid (16%), 3.5% of lauric acid, and 1.8% of heptadecanoic acid; as well as 1% (by weight) of phospholipids and about 0.3% of glycolipids. No explanation was given for these discrepancies. [7]

Related Research Articles

<span class="mw-page-title-main">Lipid</span> Substance of biological origin that is soluble in nonpolar solvents

Lipids are a broad group of organic compounds which include fats, waxes, sterols, fat-soluble vitamins, monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing energy, signaling, and acting as structural components of cell membranes. Lipids have applications in the cosmetic and food industries, and in nanotechnology.

<span class="mw-page-title-main">Triglyceride</span> Any ester of glycerol having all three hydroxyl groups esterified with fatty acids

A triglyceride is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates, as well as vegetable fat. They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver, and are a major component of human skin oils.

α-Linolenic acid Chemical compound

α-Linolenic acid, also known as alpha-Linolenic acid (ALA), is an n−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils.

<span class="mw-page-title-main">Tallow</span> Rendered form of beef or mutton fat

Tallow is a rendered form of beef or mutton suet, primarily made up of triglycerides.

<i>Triadica sebifera</i> Species of tree

Triadica sebifera is a tree native to eastern China. It is commonly called Chinese tallow, Chinese tallowtree, Florida aspen, chicken tree, gray popcorn tree, or candleberry tree.

<span class="mw-page-title-main">Oleic acid</span> Monounsaturated omega-9 fatty acid

Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid, abbreviated with a lipid number of 18:1 cis-9, and a main product of Δ9-desaturase. It has the formula CH3−(CH2)7−CH=CH−(CH2)7−COOH. The name derives from the Latin word oleum, which means oil. It is the most common fatty acid in nature. The salts and esters of oleic acid are called oleates. It is part of many oils and thus used in a lot of artificial food, as well as for soap.

<span class="mw-page-title-main">Omega-6 fatty acid</span> Fatty acids where the sixth bond is double

Omega-6 fatty acids are a family of polyunsaturated fatty acids that have in common a final carbon-carbon double bond in the n-6 position, that is, the sixth bond, counting from the methyl end.

<span class="mw-page-title-main">Drying oil</span> Oil that hardens after exposure to air

A drying oil is an oil that hardens to a tough, solid film after a period of exposure to air, at room temperature. The oil hardens through a chemical reaction in which the components crosslink by the action of oxygen. Drying oils are a key component of oil paint and some varnishes. Some commonly used drying oils include linseed oil, tung oil, poppy seed oil, perilla oil, and walnut oil. Their use has declined over the past several decades, as they have been replaced by alkyd resins and other binders.

Linoleic acid (LA) is an organic compound with the formula HOOC(CH
2)
7CH=CHCH
2CH=CH(CH
2)
4CH
3. Both alkene groups are cis. It is a fatty acid sometimes denoted 18:2 (n-6) or 18:2 cis-9,12. A linoleate is a salt or ester of this acid.

<span class="mw-page-title-main">Saponification value</span> Milligrams of a base required to saponify 1g of fat

Saponification value or saponification number represents the number of milligrams of potassium hydroxide (KOH) or sodium hydroxide (NaOH) required to saponify one gram of fat under the conditions specified. It is a measure of the average molecular weight of all the fatty acids present in the sample in form of triglycerides. The higher the saponification value, the lower the fatty acids average length, the lighter the mean molecular weight of triglycerides and vice versa. Practically, fats or oils with high saponification value are more suitable for soap making.

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Fatty acid desaturases are a family of enzymes that convert saturated fatty acids into unsaturated fatty acids and polyunsaturated fatty acids. For the common fatty acids of the C18 variety, desaturases convert stearic acid into oleic acid. Other desaturases convert oleic acid into linolenic acid, which is the precursor to alpha-linolenic acid, gamma-linolenic acid, and eicosatrienoic acid.

<span class="mw-page-title-main">Perilla oil</span>

Perilla oil is an edible vegetable oil derived from perilla seeds. Having a distinct nutty aroma and taste, the oil pressed from the toasted perilla seeds is used as a flavor enhancer, condiment, and cooking oil in Korean cuisine. The oil pressed from untoasted perilla seeds is used for non-culinary purposes.

Candlenut oil or kukui nut oil is extracted from the nut of Aleurites moluccanus, the candlenut or kuku'i.

<span class="mw-page-title-main">Cyclopropane fatty acid</span>

Cyclopropane fatty acids (CPA) are a subgroup of fatty acids that contain a cyclopropane group. Although they are usually rare, the seed oil from lychee contains nearly 40% CPAs in the form of triglycerides.

α-Parinaric acid Chemical compound

α-Parinaric acid is a conjugated polyunsaturated fatty acid. Discovered by Tsujimoto and Koyanagi in 1933, it contains 18 carbon atoms and 4 conjugated double bonds. The repeating single bond-double bond structure of α-parinaric acid distinguishes it structurally and chemically from the usual "methylene-interrupted" arrangement of polyunsaturated fatty acids that have double-bonds and single bonds separated by a methylene unit (−CH2−). Because of the fluorescent properties conferred by the alternating double bonds, α-parinaric acid is commonly used as a molecular probe in the study of biomembranes.

Vateria indica oil is extracted from the seeds of the Vateria indica plant, a species in the family Dipterocarpaceae. The Vateria indica plant is indigenous to the Western Ghats, Kerala and Tamil Nadu regions of India. It thrives in the evergreen forests, surviving up to 800 meters above sea level. Oil from the seeds of the plant is extracted through a chemical refining process which makes the plant edible.

Triadica cochinchinensis is a species of tree known as the mountain tallow tree.

Stillingia tallow or Chinese vegetable tallow is a fatty substance extracted from the coat of the seeds of Triadica sebifera or Triadica cochinchinensis. It has traditionally been used for making candles. This product must be distinguished from stillingia oil, that is extracted from the seeds of those trees.

Edible oil refining is a set of processes or treatments necessary to turn vegetable raw oil into edible oil.

References

  1. ↑ Duke, James A. (1982). "{{{section}}}". Handbook of Energy Crops. Purdue Center for New Crops.
  2. 1 2 3 4 A. Crossley and T. P. Hilditch (1950): "The component acids of some authentic and commercial stillingia oils". Journal of the Science of Food and Agriculture, volume 1, issue 10, pages 292–300. doi : 10.1002/jsfa.2740011003
  3. 1 2 J. Devine (1950): "The composition of stillingia oil and the presence therein of 2:4-decadienoic acid". Journal of the Science of Food and Agriculture, volume 1, issue 3, pages 88–92. doi : 10.1002/jsfa.2740010307
  4. ↑ FAO (1994): "Vegetable and animal oils and fats". Chapter in Definition and Classification of Commodities. Accessed on 2006-11-19.
  5. 1 2 3 4 5 B. S. J. Jeffrey F. B. Padley (1991): "Chinese vegetable tallow - Characterization and contamination by stillingia oil". Journal of the American Oil Chemists' Society, doi : 10.1007/BF02662332
  6. ↑ Hans-Joachim Esser (2002): "A revision of Triadica Lour. (Euphorbiaceae)". Harvard Papers in Botany, volume 7, issue 1, pages 17-21 (5 pages)
  7. 1 2 3 4 5 Yun Liu, Hong-lingXin, and Yun-junYan (2009): "Physicochemical properties of stillingia oil: Feasibility for biodiesel production by enzyme transesterification". Industrial Crops and Products, volume 30, issue 3, pages 431-436. doi : 10.1016/j.indcrop.2009.08.004
  8. 1 2 V. C. Batterson, and W. M. Potts (1938-11-01). "Stillingia oil". Oil & Soap. 15 (11): 295–296. doi:10.1007/BF02642910. ISSN   1558-9331. S2CID   198138852.
  9. ↑ Ya-Chi Chen, A. Zlatkis, B. S. Middleditch, J. Cowles, and W. Scheld (1987): "Lipids of contemporary stillingia oil". Chromatographia, volume 23, pages 240–242. doi : 10.1007/BF02311771
  10. 1 2 3 A. Crossley and T. P. Hilditch (1953): "The component glycerides of stillingia oil". Journal of the Science of Food and Agriculture, volume 4, pages 38–44, doi : 10.1002/jsfa.2740040107
  11. ↑ K. Aitzetmüller, Yaonian Xin, Gisela Werner, and Margaretha Grönheim (1992): "High-performance liquid chromatographic investigations of stillingia oil". Journal of Chromatography A, volume 603, issues 1–2, pages 165-173. doi : 10.1016/0021-9673(92)85358-Z
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