11-Eicosenoic acid

Last updated
Gondoic acid [1]
Eicosenoic acid.png
Names
Preferred IUPAC name
(11Z)-Icos-11-enoic acid
Other names
Gondoic acid
cis-Gondoic acid
cis-11-Eicosenoic acid
11-Eicosenoic acid
11Z-Eicosenoic acid
cis-11-Icosenoic acid
(11Z)-Icos-11-enoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h9-10H,2-8,11-19H2,1H3,(H,21,22)/b10-9- Yes check.svgY
    Key: BITHHVVYSMSWAG-KTKRTIGZSA-N Yes check.svgY
  • InChI=1/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h9-10H,2-8,11-19H2,1H3,(H,21,22)/b10-9-
    Key: BITHHVVYSMSWAG-KTKRTIGZBC
  • CCCCCCCCC=CCCCCCCCCCC(=O)O
  • O=C(O)CCCCCCCCC\C=C/CCCCCCCC
Properties
C20H38O2
Molar mass 310.51 g/mol
Density 0.883 g/mL
Melting point 23 to 24 °C (73 to 75 °F; 296 to 297 K)
Hazards
Flash point 110 °C (230 °F; 383 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

11-Eicosenoic acid, also called gondoic acid, is a monounsaturated omega-9 fatty acid found in a variety of plant oils and nuts; in particular jojoba oil. [2] It is one of a number of eicosenoic acids.

Related Research Articles

Fat Esters of three fatty acid chains and the alcohol glycerol, one of the three main macronutrients, also known as triglycerides

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 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), found in plant oils, and eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), both commonly found in marine oils. Marine algae and phytoplankton are primary sources of omega−3 fatty acids. Common sources of plant oils containing ALA include walnut, edible seeds, clary sage seed oil, algal oil, flaxseed oil, Sacha Inchi oil, Echium oil, and hemp oil, while sources of animal omega−3 fatty acids EPA and DHA include fish, fish oils, eggs from chickens, squid oils and krill oil.

Wax

Waxes are a diverse class of organic compounds that are lipophilic, malleable solids near ambient temperatures. They include higher alkanes and lipids, typically with melting points above about 40 °C (104 °F), melting to give low viscosity liquids. Waxes are insoluble in water but soluble in organic, nonpolar solvents. Natural waxes of different types are produced by plants and animals and occur in petroleum.

Essential fatty acids, or EFAs, are fatty acids that humans and other animals must ingest because the body requires them for good health but cannot synthesize them.

<i>alpha</i>-Linolenic acid Chemical compound

α-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.

Cod liver oil

Cod liver oil is a dietary supplement derived from liver of cod fish (Gadidae). As with most fish oils, it contains the omega-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). Cod liver oil also contains vitamin A and vitamin D. Historically, it was given to children because vitamin D had been shown to prevent rickets, a consequence of vitamin D deficiency.

Jojoba Species of plant

Jojoba, with the botanical name Simmondsia chinensis, and also known as goat nut,deer nut,pignut,wild hazel,quinine nut,coffeeberry, and gray box bush, is native to the Southwestern United States. Simmondsia chinensis is the sole species of the family Simmondsiaceae, placed in the order Caryophyllales.

Oleic acid 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. It has the formula CH3(CH2)7CH=CH(CH2)7COOH. 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.

Linoleic acid is an organic compound with the formula COOH(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.

Baby oil

Baby oil is, in general terms, an inert oil for the purpose of keeping skin soft and supple. It is often used on babies for the purpose of maintaining "baby-soft" skin, but it is also often used by adults for skincare and massage.

Jojoba oil Oil extracted from jojoba seeds

Jojoba oil is the liquid produced in the seed of the Simmondsia chinensis (jojoba) plant, a shrub, which is native to southern Arizona, southern California, and northwestern Mexico. The oil makes up approximately 50% of the jojoba seed by weight. The terms "jojoba oil" and "jojoba wax" are often used interchangeably because the wax visually appears to be a mobile oil, but as a wax it is composed almost entirely (~97%) of mono-esters of long-chain fatty acids and alcohols (wax ester), accompanied by only a tiny fraction of triglyceride esters. This composition accounts for its extreme shelf-life stability and extraordinary resistance to high temperatures, compared with true vegetable oils.

Omega-9 fatty acids are a family of unsaturated fatty acids which have in common a final carbon–carbon double bond in the omega−9 position; that is, the ninth bond from the methyl end of the fatty acid.

Jojoba esters are the hydrogenation or transesterification product of Jojoba oil. Jojoba Esters are commonly used in cosmetic formulations as an emollient, due to its remarkable similarity to the natural oils produced by the human skin, and its high oxidative stability. Fully hydrogenated jojoba esters are most often small beads used to exfoliate the skin.

Hydrolyzed jojoba esters are the hydrolysate of jojoba esters derived by acid, enzyme or other method of hydrolysis. Hydrolyzed jojoba esters are commonly used in cosmetic formulations.

A wax ester (WE) is an ester of a fatty acid and a fatty alcohol. Wax esters comprise the main components of three commercially important waxes: carnauba wax, candelilla wax, and beeswax.

Long-chain alcohol oxidase is one of two enzyme classes that oxidize long-chain or fatty alcohols to aldehydes. It has been found in certain Candida yeast, where it participates in omega oxidation of fatty acids to produce acyl-CoA for energy or industrial use, as well as in other fungi, plants, and bacteria.

In enzymology, a long-chain-alcohol O-fatty-acyltransferase is an enzyme that catalyzes the chemical reaction

Eicosenoic acid may refer to one of three closely related chemical compounds:

References

  1. cis-11-Eicosenoic acid at Sigma-Aldrich
  2. Miwa, Thomas (1971). "Jojoba Oil Wax Esters and Derived Fatty Acids and Alcohols: Gas Chromatographic Analyses". Journal of the American Oil Chemists' Society. 48 (6): 259–264. doi:10.1007/bf02638458. S2CID   1466516 . Retrieved May 6, 2013.CS1 maint: discouraged parameter (link)