Ximenynic acid

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Ximenynic acid
Ximenynic acid Structural Formula V.1.svg
Names
Preferred IUPAC name
(11E)-Octadec-11-en-9-ynoic acid
Other names
Santalbic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.346 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-179-1
PubChem CID
UNII
  • InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,11-17H2,1H3,(H,19,20)/b8-7+
    Key: VENIIVIRETXKSV-BQYQJAHWSA-N
  • CCCCCCC=CC#CCCCCCCCC(=O)O
Properties
C18H30O2
Molar mass 278.436 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ximenynic acid is trans-11-octadecen-9-ynoic acid, [1] a long-chain acetylenic fatty acid. [1]

Contents

It was discovered in the fruit kernels of three species of South American plants in the genus Ximenia , after which it is named. [2] and found to have the formula C18H30O2. [2]

It can be extracted from the fruit kernels of the Santalum obtusifolium (Sandalwood) [3] and the Australian sandalwood Santalum spicatum [1]

It is also found in seed oil of other plants in the Santalaceae family, including the native cherry Exocarpos cupressiformis and sweet quandong Santalum acuminatum . [4]

Sources

Species % of kernel oilNotes
S. spicatum34 [1]
S. obtusifolium71.5 [3]
S. acuminatum ?

Patents

It was the subject of a 2003 European patent (for use in food). [5] The patent application was deemed withdrawn in August 2012. [6]

Uses

It is used in some skincare products. [7] [ better source needed ]

Related Research Articles

<span class="mw-page-title-main">Sandalwood</span> Class of woods from trees in the genus Santalum

Sandalwood is a class of woods from trees in the genus Santalum. The woods are heavy, yellow, and fine-grained, and, unlike many other aromatic woods, they retain their fragrance for decades. Sandalwood oil is extracted from the woods. Sandalwood is often cited as one of the most expensive woods in the world. Both the wood and the oil produce a distinctive fragrance that has been highly valued for centuries. Consequently, some species of these slow-growing trees have suffered over-harvesting in the past.

<span class="mw-page-title-main">Palmitic acid</span> Chemical compound

Palmitic acid is a fatty acid with a 16-carbon chain. It is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is CH3(CH2)14COOH, and its C:D ratio is 16:0. It is a major component of palm oil from the fruit of Elaeis guineensis, making up to 44% of total fats. Meats, cheeses, butter, and other dairy products also contain palmitic acid, amounting to 50–60% of total fats.

Linoleic acid (LA) is an organic compound with the formula HOOC(CH2)7CH=CHCH2CH=CH(CH2)4CH3. 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.

<i>Santalum</i> Genus of flowering plant in the mistletoe family Santalaceae

Santalum is a genus of woody flowering plants in the Santalaceae family, the best known and commercially valuable of which is the Indian sandalwood tree, S. album. Members of the genus are trees or shrubs. Most are root parasites which photosynthesize their own food, but tap the roots of other species for water and inorganic nutrients. Several species, most notably S. album, produce highly aromatic wood, used for scents and perfumes and for herbal medicine. About 25 known species range across the Indomalayan, Australasian, and Oceanian realms, from India through Malesia to the Pacific Islands, as far as Hawaiʻi and the Juan Fernández Islands off the coast of South America.

<i>Santalum acuminatum</i> Species of plant

Santalum acuminatum, the desert quandong, is a hemiparasitic plant in the sandalwood family, Santalaceae, which is widely dispersed throughout the central deserts and southern areas of Australia. The species, especially its edible fruit, is also commonly referred to as quandong or native peach. The use of the fruit as an exotic flavouring, one of the best known bush tucker, has led to the attempted domestication of the species.

<i>Attalea maripa</i> Species of palm

Attalea maripa, commonly called maripa palm is a palm native to tropical South America and Trinidad and Tobago. It grows up 35 m (115 ft) tall and can have leaves or fronds 10–12 m (33–39 ft) long. This plant has a yellow edible fruit which is oblong ovoid and cream. An edible oil can be extracted from the pulp of the fruit and from the kernel of the seed.

<i>Santalum spicatum</i> Australian sandalwood

Santalum spicatum, the Australian sandalwood, also Waang and other names (Noongar) and Dutjahn (Martu), is a tree native to semi-arid areas at the edge of Southwest Australia, in the state of Western Australia. It is also found in South Australia, where it is protected and listed as a vulnerable species. It is traded as sandalwood, and its sandalwood oil has been used as an aromatic and a food source over history. S. spicatum is one of four Santalum species occurring in Australia.

<span class="mw-page-title-main">Sea buckthorn oil</span> Vegetable oil

Sea buckthorn oil is a red-orange oil derived from sea buckthorn plants. The most commonly used species for this purpose is Hippophae rhamnoides. Species belonging to this genus accumulate lipids in the mesocarp, so the oil can be extracted from either the seeds or the pulp.

<span class="mw-page-title-main">Ricinoleic acid</span> Chemical compound

Ricinoleic acid, formally called 12-hydroxy-9-cis-octadecenoic acid, is a fatty acid. It is an unsaturated omega-9 fatty acid and a hydroxy acid. It is a major component of the seed oil obtained from the seeds of castor plant, the plant that produces ricin. It is also found in the sclerotium of ergot. About 90% of the fatty acid content in castor oil is the ricinolein.

<i>Santalum album</i> Species of tree in Sandalwood family

Santalum album, or Indian sandalwood, is a small tropical tree, and the traditional source of sandalwood oil. It is native to southern India and Southeast Asia. It is considered sacred in some religions like Hinduism, and some cultures place great significance on its fragrant qualities. However, the high value of the species has caused over-exploitation, to the point where the wild population is vulnerable to extinction. Indian sandalwood still commands high prices for its essential oil owing to its high alpha santalol content, but due to lack of sizable trees it is no longer used for fine woodworking as before. The plant is long-lived, but harvest is only viable after many years.

<i>Dacryodes edulis</i> Species of tree

Dacryodes edulis is a fruit tree in the Burseraceae family native to Africa. Its various regional names include safou, messa, plum (Cameroon), atanga, ube, elumi (Nigeria), African pear, bush pear, African plum, nsafu, bush butter tree, or butterfruit.

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

Marula oil is extracted from the kernels (nuts) of the fruits of the Marula tree, from the family Anacardiaceae. There are two types of marula oil, the oil extracted from the seeds and the oil extracted from the nut's hard shell. Marula oil is traditionally used in cosmetics, in food as a cooking oil and meat preservative and to treat leather. Marula oil can also be used as body lotion. In Namibia Marula fruit is processed into a range of juices, jellies and jams.

Oleochemistry is the study of vegetable oils and animal oils and fats, and oleochemicals derived from these fats and oils. The resulting product can be called oleochemicals (from Latin: oleum "olive oil"). The major product of this industry is soap, approximately 8.9×106 tons of which were produced in 1990. Other major oleochemicals include fatty acids, fatty acid methyl esters, fatty alcohols and fatty amines. Glycerol is a side product of all of these processes. Intermediate chemical substances produced from these basic oleochemical substances include alcohol ethoxylates, alcohol sulfates, alcohol ether sulfates, quaternary ammonium salts, monoacylglycerols (MAG), diacylglycerols (DAG), structured triacylglycerols (TAG), sugar esters, and other oleochemical products.

Sandalwood is the common name of many species of plants and their wood and oils.

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

Sandalwood oil is an essential oil obtained from the steam distillation of chips and billets cut from the heartwood of various species of sandalwood trees, mainly Santalum album and Santalum spicatum.

<i>Santalum austrocaledonicum</i> Species of tree

Santalum austrocaledonicum, or New Caledonia sandalwood, is a sandalwood tree from the family Santalaceae. It is a small tree with gray bark and green leaves, and is parasitic. Most have been removed from their habitat due to logging; very few trees remain in the wild.

<i>Santalum obtusifolium</i> Species of shrub

Santalum obtusifolium, known as the sandalwood or blunt sandalwood, is a shrub found in eastern Australia. Often seen around a metre tall, it may grow to 2.5 metres high. Seen in eucalyptus forests and woodlands, often by creeks and usually not far from the sea. It grows in moderate to high rainfall areas such as Royal and Lamington National Parks. Growing as far from the coast as Yarrowitch, Megalong Valley and Braidwood in New South Wales.

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

Tamanu oil is pressed from nuts of either Calophyllum inophyllum (usually) or Calophyllum tacamahaca (ati), tropical trees belonging to the Calophyllaceae family. The oil originates in Polynesia, where it continues to play an important cultural role.

Tariric acid is an acetylenic fatty acid that can be found in the tallow-wood tree, Ximenia americana.

References

  1. 1 2 3 4 Liu, Yandi D.; Longmore, Robert B.; Fox, John E. D. (December 1996). "Separation and identification of ximenynic acid isomers in the seed oil of Santalum spicatum R.Br. as their 4,4-dimethyloxazoline derivatives". Journal of the American Oil Chemists' Society. 73 (12): 1729–1731. doi:10.1007/BF02517979. ISSN   0003-021X. S2CID   83483921.
  2. 1 2 Lightelm, S. P.; Schwartz, H. M.; von Holdt, M. M. (1952). "193. The chemistry of ximenynic acid". Journal of the Chemical Society (Resumed): 1088. doi:10.1039/jr9520001088. ISSN   0368-1769.
  3. 1 2 Medicinal Plants in Australia, Volume 1. Cheryll Williams page 274. ISBN   978-1-877058-79-0
  4. Okada, Shoko; Zhou, Xue-Rong; Damcevski, Katherine; Gibb, Nerida; Wood, Craig; Hamberg, Mats; Haritos, Victoria S. (November 2013). "Diversity of Δ12 Fatty Acid Desaturases in Santalaceae and Their Role in Production of Seed Oil Acetylenic Fatty Acids". Journal of Biological Chemistry. 288 (45): 32405–32413. doi: 10.1074/jbc.M113.511931 . PMC   3820875 . PMID   24062307.
  5. EP 1402787 A1:Ximenynic acid
  6. Ximenynic acid
  7. Sandalwood Nut CO2 Oil (product)