Sapienic acid

Last updated
Sapienic acid
Sapienic acid.svg
Names
Preferred IUPAC name
(6Z)-Hexadec-6-enoic acid
Other names
cis-6-Hexadecenoic acid
16:1ω10
16:1n10 (lipid numbers)
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h10-11H,2-9,12-15H2,1H3,(H,17,18)/b11-10- X mark.svgN
    Key: NNNVXFKZMRGJPM-KHPPLWFESA-N X mark.svgN
  • InChI=1/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h10-11H,2-9,12-15H2,1H3,(H,17,18)/b11-10-
    Key: NNNVXFKZMRGJPM-KHPPLWFEBD
  • O=C(O)CCCC\C=C/CCCCCCCCC
Properties
C16H30O2
Molar mass 254.414 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Sapienic acid is a fatty acid that is a major component of human sebum. Unique to humans, it takes its scientific name from the root sapiens. The equivalent fatty acid in mouse sebum is palmitoleic acid. [1] Sapienic acid salts, esters, anion, and conjugate base are known as sapienates.

Deficient production of sapienic acid has been implicated in the development of atopic dermatitis, [2] and sapienic acid has potent antibacterial activity against pathogens like Staphylococcus aureus. [3] [4] Reduced omega-3 intake has been linked to lower sapienic acid levels in sebum. [5]

Delta-6-desaturation of palmitic acid leads to the biosynthesis of sapienic acid. In other tissues linoleic acid is the target for delta 6 desaturase, but linoleic acid is degraded in sebaceous cells, allowing the enzyme to desaturate palmitic to sapienic acid. [6] [7] A two-carbon extension product of sapienic acid, sebaleic acid, is also present in sebum. Sapienic acid can lead to the decanal which is likely what mosquitoes use to identify human prey. [8]

Related Research Articles

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.

<span class="mw-page-title-main">Dandruff</span> Skin condition of the scalp

Dandruff is a skin condition that mainly affects the scalp. Symptoms include flaking and sometimes mild itchiness. It can result in social or self-esteem problems. A more severe form of the condition, which includes inflammation of the skin, is known as seborrhoeic dermatitis.

<span class="mw-page-title-main">Sebaceous gland</span> Gland to lubricate the hair and skin

A sebaceous gland, or oil gland, is a microscopic exocrine gland in the skin that opens into a hair follicle to secrete an oily or waxy matter, called sebum, which lubricates the hair and skin of mammals. In humans, sebaceous glands occur in the greatest number on the face and scalp, but also on all parts of the skin except the palms of the hands and soles of the feet. In the eyelids, meibomian glands, also called tarsal glands, are a type of sebaceous gland that secrete a special type of sebum into tears. Surrounding the female nipple, areolar glands are specialized sebaceous glands for lubricating the nipple. Fordyce spots are benign, visible, sebaceous glands found usually on the lips, gums and inner cheeks, and genitals.

<i>Cutibacterium acnes</i> Species of bacterium

Cutibacterium acnes is the relatively slow-growing, typically aerotolerant anaerobic, gram-positive bacterium (rod) linked to the skin condition of acne; it can also cause chronic blepharitis and endophthalmitis, the latter particularly following intraocular surgery. Its genome has been sequenced and a study has shown several genes can generate enzymes for degrading skin and proteins that may be immunogenic.

Linoleic acid (LA) is an organic compound with the formula HOOC(CH
2
)
7
CH=CHCH
2
CH=CH(CH
2
)
4
CH
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">Sebacic acid</span> Chemical compound

Sebacic acid is a naturally occurring dicarboxylic acid with the chemical formula HO2C(CH2)8CO2H. It is a white flake or powdered solid. Sebaceus is Latin for tallow candle, sebum is Latin for tallow, and refers to its use in the manufacture of candles. Sebacic acid is a derivative of castor oil.

Skin disorders are among the most common health problems in dogs, and have many causes. The condition of a dog's skin and coat is also an important indicator of its general health. Skin disorders of dogs vary from acute, self-limiting problems to chronic or long-lasting problems requiring life-time treatment. Skin disorders may be primary or secondary in nature, making diagnosis complicated.

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

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, fatty fish, fish oil, or algae oil.

Dihomo-γ-linolenic acid (DGLA) is a 20-carbon ω−6 fatty acid. In physiological literature, it is given the name 20:3 (ω−6). DGLA is a carboxylic acid with a 20-carbon chain and three cis double bonds; the first double bond is located at the sixth carbon from the omega end. DGLA is the elongation product of γ-linolenic acid. GLA, in turn, is a desaturation product of linoleic acid. DGLA is made in the body by the elongation of GLA, by an efficient enzyme which does not appear to suffer any form of (dietary) inhibition. DGLA is an extremely uncommon fatty acid, found only in trace amounts in animal products.

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">Essential fatty acid interactions</span>

There are many fatty acids found in nature. Two types of fatty acids considered essential for human health are the omega-3 and omega-6 types. These two essential fatty acids are necessary for some cellular signalling pathways and are involved in mediating inflammation, protein synthesis, and metabolic pathways in the human body.

Vaccenic acid is a naturally occurring trans fatty acid and an omega-7 fatty acid. It is the predominant kind of trans-fatty acid found in human milk, in the fat of ruminants, and in dairy products such as milk, butter, and yogurt. Trans fat in human milk may depend on trans fat content in food.

In biochemistry, 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 surrounds the organelles within the cells. In addition to cytosolic fatty acid synthesis, there is also mitochondrial fatty acid synthesis (mtFASII), in which malonyl-CoA is formed from malonic acid with the help of malonyl-CoA synthetase (ACSF3), which then becomes the final product octanoyl-ACP (C8) via further intermediate steps.

<span class="mw-page-title-main">Acyl-(acyl-carrier-protein) desaturase</span> Class of enzymes

In enzymology, an acyl-[acyl-carrier-protein] desaturase (EC 1.14.19.2) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Linoleoyl-CoA desaturase</span> Class of enzymes

Linoleoyl-CoA desaturase (also Delta 6 desaturase, EC 1.14.19.3) is an enzyme that converts between types of fatty acids, which are essential nutrients in the human body. The enzyme mainly catalyzes the chemical reaction

<span class="mw-page-title-main">Stearoyl-CoA 9-desaturase</span> Class of enzymes

Stearoyl-CoA desaturase (Δ-9-desaturase) is an endoplasmic reticulum enzyme that catalyzes the rate-limiting step in the formation of monounsaturated fatty acids (MUFAs), specifically oleate and palmitoleate from stearoyl-CoA and palmitoyl-CoA. Oleate and palmitoleate are major components of membrane phospholipids, cholesterol esters and alkyl-diacylglycerol. In humans, the enzyme is encoded by the SCD gene.

<span class="mw-page-title-main">FADS2</span> Protein-coding gene in the species Homo sapiens

Fatty acid desaturase 2 (FADS2) is an enzyme that in humans is encoded by the FADS2 gene.

<span class="mw-page-title-main">Melanocortin 5 receptor</span> Protein-coding gene in the species Homo sapiens

Melanocortin 5 receptor (MC5R) is a protein that in humans is encoded by the MC5R gene. It is located on the chromosome 18 in the human genome. When the MC5R was disrupted in transgenic mice, it induced disruption of their exocrine glands and resulted in decreased production of sebum.

<span class="mw-page-title-main">Pimple</span> Type of comedo

A pimple or zit is a kind of comedo that results from excess sebum and dead skin cells getting trapped in the pores of the skin. In its aggravated state, it may evolve into a pustule or papule. Pimples can be treated by acne medications, antibiotics, and anti-inflammatories prescribed by a physician, or various over the counter remedies purchased at a pharmacy.

Infantile acne is a form of acneiform eruption that occurs in infants from 6 weeks to 1 year of age. Typical symptoms include inflammatory and noninflammatory lesions, papules and pustules most commonly present on the face. No cause of infantile acne has been established but it may be caused by increased sebaceous gland secretions due to elevated androgens, genetics and the fetal adrenal gland causing increased sebum production. Infantile acne can resolve by itself by age 1 or 2. However, treatment options include topical benzyl peroxide, topical retinoids and topical antibiotics in most cases.

References

  1. Katsuta Y, Iida T, Inomata S, Denda M (May 2005). "Unsaturated fatty acids induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis". The Journal of Investigative Dermatology. Nature Publishing Group. 124 (5): 1008–13. doi: 10.1111/j.0022-202X.2005.23682.x . PMID   15854043.
  2. Takigawa H, Nakagawa H, Kuzukawa M, Mori H, Imokawa G (2005). "Deficient production of hexadecenoic acid in the skin is associated in part with the vulnerability of atopic dermatitis patients to colonization by Staphylococcus aureus". Dermatology. 211 (3): 240–8. doi:10.1159/000087018. PMID   16205069. S2CID   1574784.
  3. Webster GF, Anthony V. Rawlings (2007). Acne and Its Therapy. Basic and clinical dermatology. Vol. 40. CRC Press. p. 311. ISBN   978-0-8247-2971-4.
  4. Neumann Y, Ohlsen K, Donat S, Engelmann S, Kusch H, Albrecht D, et al. (March 2015). "The effect of skin fatty acids on Staphylococcus aureus". Archives of Microbiology. 197 (2): 245–67. Bibcode:2015ArMic.197..245N. doi:10.1007/s00203-014-1048-1. PMC   4326651 . PMID   25325933.
  5. Park HG, Kothapalli KS, Park WJ, DeAllie C, Liu L, Liang A, et al. (February 2016). "Palmitic acid (16:0) competes with omega-6 linoleic and omega-3 ɑ-linolenic acids for FADS2 mediated Δ6-desaturation". Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 1861 (2): 91–97. doi:10.1016/j.bbalip.2015.11.007. PMC   4691389 . PMID   26597785.
  6. Pappas A, Anthonavage M, Gordon JS (January 2002). "Metabolic fate and selective utilization of major fatty acids in human sebaceous gland". The Journal of Investigative Dermatology. Nature Publishing Group. 118 (1): 164–71. doi: 10.1046/j.0022-202x.2001.01612.x . PMID   11851890.
  7. Ge L, Gordon JS, Hsuan C, Stenn K, Prouty SM (May 2003). "Identification of the delta-6 desaturase of human sebaceous glands: expression and enzyme activity". The Journal of Investigative Dermatology. Nature Publishing Group. 120 (5): 707–14. doi: 10.1046/j.1523-1747.2003.12123.x . PMID   12713571.
  8. Zhao Z, Zung JL, Kriete AL, Iqbal A, Younger MA, Matthews BJ, Merhof D, Thiberge S, Strauch M, McBride CS (2020). "Chemical signatures of human odour generate a unique neural code in the brain of Aedes aegypti mosquitoes" (PDF). doi:10.1101/2020.11.01.363861. S2CID   226263862.{{cite journal}}: Cite journal requires |journal= (help)