Names | |
---|---|
IUPAC name 13-[(1S)-Cyclopent-2-en-1-yl]tridecanoic acid | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.044.931 |
EC Number |
|
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C18H32O2 | |
Molar mass | 280.452 g·mol−1 |
Melting point | 68.5 °C (155.3 °F; 341.6 K) [1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Chaulmoogric acid is a fatty acid found chaulmoogra oil, the oil from the seeds of Hydnocarpus wightianus . [2] It is an unusual fatty acid which has a cyclopentene ring at its terminus instead of being entirely linear like most fatty acids. [3]
It is a white crystalline solid with a melting point of 68.5 °C. [1] It is soluble in ether, chloroform, and ethyl acetate. [1]
In the early 20th century, it was investigated as a possible treatment for leprosy due to the use in traditional medicine of chaulmoogra oil for leprosy. [4]
In nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such compounds, most commonly those that occur in living beings or in food.
Omega−3 fatty acids. , also called Omega−3 oils, ω−3 fatty acids, Ω-3 Fatty acids or n−3 fatty acids, are polyunsaturated fatty acids (PUFAs) characterized by the presence of a double bond three atoms away from the terminal methyl group in their chemical structure. They are widely distributed in nature, being important constituents of animal lipid metabolism, and they play an important role in the human diet and in human physiology. The three types of omega−3 fatty acids involved in human physiology are α-linolenic acid (ALA), eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). ALA can be found in plants, while DHA and EPA are found in algae and fish. Marine algae and phytoplankton are primary sources of omega−3 fatty acids. DHA and EPA accumulate in fish that eat these algae. Common sources of plant oils containing ALA include walnuts, edible seeds, and flaxseeds as well as hempseed oil, while sources of EPA and DHA include fish and fish oils, and algae oil.
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.
A saturated fat is a type of fat in which the fatty acid chains have all single bonds between the carbon atoms. A fat known as a glyceride is made of two kinds of smaller molecules: a short glycerol backbone and fatty acids that each contain a long linear or branched chain of carbon (C) atoms. Along the chain, some carbon atoms are linked by single bonds (-C-C-) and others are linked by double bonds (-C=C-). A double bond along the carbon chain can react with a pair of hydrogen atoms to change into a single -C-C- bond, with each H atom now bonded to one of the two C atoms. Glyceride fats without any carbon chain double bonds are called saturated because they are "saturated with" hydrogen atoms, having no double bonds available to react with more hydrogen.
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 due to the presence of impurities. 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 a common component of oils, and thus occurs in many types of food, as well as in soap.
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.
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.
Fish oil is oil derived from the tissues of oily fish. Fish oils contain the omega-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), precursors of certain eicosanoids that are known to reduce inflammation in the body and improve hypertriglyceridemia. There has been a great deal of controversy in the 21st century about the role of fish oil in cardiovascular disease, with recent meta-analyses reaching different conclusions about its potential impact.
In biochemistry and nutrition, a monounsaturated fat is a fat that contains a monounsaturated fatty acid (MUFA), a subclass of fatty acid characterized by having a double bond in the fatty acid chain with all of the remaining carbon atoms being single-bonded. By contrast, polyunsaturated fatty acids (PUFAs) have more than one double bond.
Docosahexaenoic acid (DHA) is an omega-3 fatty acid that is an important component of the human brain, cerebral cortex, skin, and retina. It is given the fatty acid notation 22:6(n-3). It can be synthesized from alpha-linolenic acid or obtained directly from maternal milk, fatty fish, fish oil, or algae oil. The consumption of DHA contributes to numerous physiological benefits, including cognition. As a component of neuronal membranes, the function of DHA is to support neuronal conduction and to allow the optimal functioning of neuronal membrane proteins.
Hydnocarpus kurzii is a species of plant in the family Achariaceae. It is found in India and Myanmar.
A very-long-chain fatty acid (VLCFA) is a fatty acid with 22 or more carbons. Their biosynthesis occurs in the endoplasmic reticulum. VLCFA's can represent up to a few percent of the total fatty acid content of a cell.
Gynocardia is a genus of dioecious evergreen tree belonging to the Achariaceae family, containing the sole species Gynocardia odorata. The trees grow up to 30 m tall. The species is found in moist forests of mountain valleys in South Asia - India, South-east Tibet and Yunnan in China, Bangladesh, Nepal, Bhutan and Myanmar.
Hydnocarpus wightianus or chaulmoogra is a tree in the Achariaceae family. Hydnocarpus wightiana seed oil has been widely used in traditional Indian medicine, especially in Ayurveda, and in Chinese traditional medicine for the treatment of leprosy. It entered early Western medicine in the nineteenth century before the era of sulfonamides and other antibiotics for the treatment of several skin diseases and leprosy. The oil was prescribed for leprosy as a mixture suspended in gum or as an emulsion.
The history of leprosy was traced to its origins by an international team of 22 geneticists using comparative genomics of the worldwide distribution of Mycobacterium leprae. Monot et al. (2005) determined that leprosy originated in East Africa or the Near East and traveled with humans along their migration routes, including those of trade in goods and slaves. The four strains of M. leprae are based in specific geographic regions where each predominantly occurs:
Alice Augusta Ball was an American chemist who developed the "Ball Method" for making ethyl ester derivatives of chaulmoogra oil, which were used as a treatment for leprosy during the early 20th century. She was the first woman and first African American to receive a master's degree from the University of Hawaiʻi, and was also the university's first female and African American chemistry professor. She died at age 24 and her contributions to science were not recognized until many years after her death.
Hydnocarpic acid is an unsaturated fatty acid. It differs from most fatty acids by having a cyclic ring system at the terminus, rather than being entirely straight chain. It is found in the oil from plants of the genus Hydnocarpus from which it derives its name.
Frederick Belding Power was an American chemist who worked in pharmacology, plant chemicals, and on standards in pharmaceutical production. He served as a professor of pharmacy at the Philadelphia College and as director of pharmacy at the University of Wisconsin–Madison. He also served as a chemist for the Wellcome Chemical Research Laboratories in London where he examined Chaulmoogra oil and its use in the treatment of leprosy.
Ernest Muir FRCS, CIE, CMG was a Scottish medical missionary and educator in British-controlled India and Nigeria most noted for his work with Hansen's disease (leprosy).