Prostanoic acid

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Prostanoic acid
Prostanoic acid Structure.svg
Names
IUPAC name
7-[(1S,2S)-2-octylcyclopentyl]heptanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
  • InChI=1S/C20H38O2/c1-2-3-4-5-6-9-13-18-15-12-16-19(18)14-10-7-8-11-17-20(21)22/h18-19H,2-17H2,1H3,(H,21,22)/t18-,19-/m0/s1
    Key: WGJJROVFWIXTPA-OALUTQOASA-N
  • CCCCCCCCC1CCCC1CCCCCCC(=O)O
Properties
C20H38O2
Molar mass 310.522 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Prostanoic acid (7-[(1S,2S)-2-octylcyclopentyl]heptanoic acid) is a saturated fatty acid which contains a cyclopentane ring. Its derivatives are prostaglandins - physiologically active lipid substances. Prostanoic acid is not found in nature, but it can be synthesized in vitro.

Contents

Synthesis

For the first time the synthesis of prostanoic acid from 1-formylcyclopentene was considered in detail in the scientific literature in 1975 by a group of French pharmacists. [1] One year later, a group of Japanese scientists, who worked in the central research laboratory of the "Sankyo Co., Ltd." company (Shinagawa, Tokyo), published another method for obtaining prostanoic acid from 2-[4-hydroxy-5-(methoxymethyl)cyclopent-2-en-1-yl] acetic acid. [2] In 1986, a group of Japanese scientists from Kyushu University in Fukuoka proposed their own scheme for obtaining prostanoic acid from limonene. [3]

See also

Related Research Articles

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Prostaglandin Group of physiologically active lipid compounds

The prostaglandins (PG) are a group of physiologically active lipid compounds called eicosanoids having diverse hormone-like effects in animals. Prostaglandins have been found in almost every tissue in humans and other animals. They are derived enzymatically from the fatty acid arachidonic acid. Every prostaglandin contains 20 carbon atoms, including a 5-carbon ring. They are a subclass of eicosanoids and of the prostanoid class of fatty acid derivatives.

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Arachidonic acid Fatty acid used metabolically in many organisms

Arachidonic acid is a polyunsaturated omega-6 fatty acid 20:4(ω-6), or 20:4(5,8,11,14). It is structurally related to the saturated arachidic acid found in cupuaçu butter. Its name derives from the New Latin word arachis (peanut), but it is important to note that peanut oil does not contain any arachidonic acid.

Eicosanoid

Eicosanoids are signaling molecules made by the enzymatic or non-enzymatic oxidation of arachidonic acid or other polyunsaturated fatty acids (PUFAs) that are, similar to arachidonic acid, 20 carbon units in length. Eicosanoids are a sub-category of oxylipins, i.e. oxidized fatty acids of diverse carbon units in length, and are distinguished from other oxylipins by their overwhelming importance as cell signaling molecules. Eicosanoids function in diverse physiological systems and pathological processes such as: mounting or inhibiting inflammation, allergy, fever and other immune responses; regulating the abortion of pregnancy and normal childbirth; contributing to the perception of pain; regulating cell growth; controlling blood pressure; and modulating the regional flow of blood to tissues. In performing these roles, eicosanoids most often act as autocrine signaling agents to impact their cells of origin or as paracrine signaling agents to impact cells in the proximity of their cells of origin. Eicosanoids may also act as endocrine agents to control the function of distant cells.

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.

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Docosahexaenoic acid

Docosahexaenoic acid (DHA) is an omega-3 fatty acid that is a primary structural component of the human brain, cerebral cortex, skin, and retina. In physiological literature, it is given the name 22:6(n-3). It can be synthesized from alpha-linolenic acid or obtained directly from maternal milk, fish oil, or algae oil.

Glycerophospholipid

Glycerophospholipids or phosphoglycerides are glycerol-based phospholipids. They are the main component of biological membranes.

Chiral auxiliary

A chiral auxiliary is a stereogenic group or unit that is temporarily incorporated into an organic compound in order to control the stereochemical outcome of the synthesis. The chirality present in the auxiliary can bias the stereoselectivity of one or more subsequent reactions. The auxiliary can then be typically recovered for future use.

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Sphingosine kinase

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Docosatetraenoic acid

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Fatty acid synthase

Fatty acid synthase (FAS) is an enzyme that in humans is encoded by the FASN gene.

Fatty acid synthesis is the creation of fatty acids from acetyl-CoA and NADPH through the action of enzymes called fatty acid synthases. This process takes place in the cytoplasm of the cell. Most of the acetyl-CoA which is converted into fatty acids is derived from carbohydrates via the glycolytic pathway. The glycolytic pathway also provides the glycerol with which three fatty acids can combine to form triglycerides, the final product of the lipogenic process. When only two fatty acids combine with glycerol and the third alcohol group is phosphorylated with a group such as phosphatidylcholine, a phospholipid is formed. Phospholipids form the bulk of the lipid bilayers that make up cell membranes and surround the organelles within the cells

Free fatty acid receptor 1

Free fatty acid receptor 1 (FFA1), also known as GPR40, is a class A G-protein coupled receptor that in humans is encoded by the FFAR1 gene. It is strongly expressed in the cells of the pancreas and to a lesser extent in the brain. This membrane protein binds free fatty acids, acting as a nutrient sensor for regulating energy homeostasis.

CYP4A11

Cytochrome P450 4A11 is a protein that in humans is codified by the CYP4A11 gene.

CYP4F8

Cytochrome P450 4F8 is a protein that in humans is encoded by the CYP4F8 gene.

CYP4F12

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Depside

A depside is a type of polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond. Depsides are most often found in lichens, but have also been isolated from higher plants, including species of the Ericaceae, Lamiaceae, Papaveraceae and Myrtaceae.

References

  1. Hamon A; Lacoume B; Olivier A; Pilgrim W.R. (November 1975). "Synthesis of prostanoic acid". Tetrahedron Letters. 16 (50): 4481–4482. doi:10.1016/S0040-4039(00)91098-0.
  2. Sakai K, Inouye K, Nakamura N (September 1976). "Synthesis of (+)-prostanoic acid (1)". Prostaglandins. 12 (3): 399–401. doi:10.1016/0090-6980(76)90020-4. PMID   968053.
  3. Suemune H, Kawahara T, Sakai K (February 1986). "Conversion of limonene to prostanoic acid and 8-isoprostanoic acid". Chemical and Pharmaceutical Bulletin. 34 (2): 550–557. doi: 10.1248/cpb.34.550 .