5Beta-Scymnol

Last updated
5Beta-Scymnol
5beta-Scymnol.png
Names
IUPAC name
(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(2R,5R)-5,7-Dihydroxy-6-(hydroxymethyl)heptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7,12-triol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
  • InChI=1S/C27H48O6/c1-15(4-7-22(31)16(13-28)14-29)19-5-6-20-25-21(12-24(33)27(19,20)3)26(2)9-8-18(30)10-17(26)11-23(25)32/h15-25,28-33H,4-14H2,1-3H3/t15-,17+,18-,19-,20+,21+,22-,23-,24+,25+,26+,27-/m1/s1
    Key: DIPHJTHZUWDJIK-JPLAUYQNSA-N
  • C[C@H](CC[C@H](C(CO)CO)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
Properties
C27H48O6
Molar mass 468.675 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

5Beta-Scymnol, also known simply as scymnol, is a synthetic INCI-listed skin conditioning ingredient. [1] [2] [3] The molecule is a steroid derivative that behaves as a hydroxyl radical scavenger and is used for the treatment of skin blemishes such as blocked pores and acne. [4] [5]

Contents

History

The molecule was identified and isolated from shark tissues by Professor Takuo Kosuge, Shizuoka College of Pharmacy, Shizuoka, Japan during the 1980s. [4] Based on usage as a traditional folk remedy, it was hypothesised the ingredient may be effective for the treatment of scalds, blemishes and acne. [6] [7] [8]

Traits

5Beta-Scymnol is a hydroxyl (OH) free radical scavenger. [5] Scymnol's role in quenching free radicals may play a role in inhibiting acne. [8] [9]

Related Research Articles

<span class="mw-page-title-main">Acne</span> Skin condition characterized by pimples

Acne, also known as acne vulgaris, is a long-term skin condition that occurs when dead skin cells and oil from the skin clog hair follicles. Typical features of the condition include blackheads or whiteheads, pimples, oily skin, and possible scarring. It primarily affects skin with a relatively high number of oil glands, including the face, upper part of the chest, and back. The resulting appearance can lead to lack of confidence, anxiety, reduced self-esteem, and, in extreme cases, depression or thoughts of suicide.

<span class="mw-page-title-main">Scar</span> Area of fibrous tissue that replaces normal skin after an injury

A scar is an area of fibrous tissue that replaces normal skin after an injury. Scars result from the biological process of wound repair in the skin, as well as in other organs, and tissues of the body. Thus, scarring is a natural part of the healing process. With the exception of very minor lesions, every wound results in some degree of scarring. An exception to this are animals with complete regeneration, which regrow tissue without scar formation.

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

Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of female reproductive cycles such as estrous and menstrual cycles. Estradiol is responsible for the development of female secondary sexual characteristics such as the breasts, widening of the hips and a female-associated pattern of fat distribution. It is also important in the development and maintenance of female reproductive tissues such as the mammary glands, uterus and vagina during puberty, adulthood and pregnancy. It also has important effects in many other tissues including bone, fat, skin, liver, and the brain.

<span class="mw-page-title-main">Melatonin</span> Hormone released by the pineal gland

Melatonin is a natural compound, specifically an indoleamine, produced by and found in different organisms including bacteria and eukaryotes. It was discovered by Aaron B. Lerner and colleagues in 1958 as a substance of the pineal gland from cows that could induce skin lightening in common frogs. It was subsequently discovered as a hormone released in the brain at night which controls the sleep–wake cycle in vertebrates.

<span class="mw-page-title-main">Photodynamic therapy</span> Form of phototherapy

Photodynamic therapy (PDT) is a form of phototherapy involving light and a photosensitizing chemical substance used in conjunction with molecular oxygen to elicit cell death (phototoxicity).

<span class="mw-page-title-main">Benzalkonium chloride</span> Surfactant and antiseptic agent

Benzalkonium chloride, also known as alkyldimethylbenzylammonium chloride (ADBAC) and by the trade name Zephiran, is a type of cationic surfactant. It is an organic salt classified as a quaternary ammonium compound. ADBACs have three main categories of use: as a biocide, a cationic surfactant, and a phase transfer agent. ADBACs are a mixture of alkylbenzyldimethylammonium chlorides, in which the alkyl group has various even-numbered alkyl chain lengths.

<span class="mw-page-title-main">Hidradenitis suppurativa</span> Human disease

Hidradenitis suppurativa (HS), sometimes known as acne inversa or Verneuil's disease, is a long-term dermatological condition characterized by the occurrence of inflamed and swollen lumps. These are typically painful and break open, releasing fluid or pus. The areas most commonly affected are the underarms, under the breasts, and the groin. Scar tissue remains after healing. HS may significantly limit many everyday activities, for instance, walking, hugging, moving, and sitting down. Sitting disability may occur in patients with lesions in sacral, gluteal, perineal, femoral, groin or genital regions; and prolonged periods of sitting down can also worsen the condition of the skin of these patients.

<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.

<span class="mw-page-title-main">Doxycycline</span> Tetracycline-class antibiotic

Doxycycline is a broad-spectrum antibiotic of the tetracycline class used in the treatment of infections caused by bacteria and certain parasites. It is used to treat bacterial pneumonia, acne, chlamydia infections, Lyme disease, cholera, typhus, and syphilis. It is also used to prevent malaria. Doxycycline may be taken by mouth or by injection into a vein.

<span class="mw-page-title-main">Hyperpigmentation</span> Darkening of an area of skin or nails caused by increased melanin

Hyperpigmentation is the darkening of an area of skin or nails caused by increased melanin.

<span class="mw-page-title-main">5α-Reductase</span> Enzyme family

5α-Reductases, also known as 3-oxo-5α-steroid 4-dehydrogenases, are enzymes involved in steroid metabolism. They participate in three metabolic pathways: bile acid biosynthesis, androgen and estrogen metabolism. There are three isozymes of 5α-reductase encoded by the genes SRD5A1, SRD5A2, and SRD5A3.

<i>Staphylococcus epidermidis</i> Species of bacterium

Staphylococcus epidermidis is a Gram-positive bacterium, and one of over 40 species belonging to the genus Staphylococcus. It is part of the normal human microbiota, typically the skin microbiota, and less commonly the mucosal microbiota and also found in marine sponges. It is a facultative anaerobic bacteria. Although S. epidermidis is not usually pathogenic, patients with compromised immune systems are at risk of developing infection. These infections are generally hospital-acquired. S. epidermidis is a particular concern for people with catheters or other surgical implants because it is known to form biofilms that grow on these devices. Being part of the normal skin microbiota, S. epidermidis is a frequent contaminant of specimens sent to the diagnostic laboratory.

<span class="mw-page-title-main">Bile acid</span> Steroid acid found predominantly in the bile of mammals and other vertebrates

Bile acids are steroid acids found predominantly in the bile of mammals and other vertebrates. Diverse bile acids are synthesized in the liver. Bile acids are conjugated with taurine or glycine residues to give anions called bile salts.

Skin care or skincare is a range of practices that support skin integrity, enhance its appearance, and relieve skin conditions. They can include nutrition, avoidance of excessive sun exposure, and appropriate use of emollients. Practices that enhance appearance include the use of cosmetics, botulinum, exfoliation, fillers, laser resurfacing, microdermabrasion, peels, retinol therapy, and ultrasonic skin treatment. Skin care is a routine daily procedure in many settings, such as skin that is either too dry or too moist, and prevention of dermatitis and prevention of skin injuries.

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

Fluoxymesterone, sold under the brand names Halotestin and Ultandren among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, breast cancer in women, and anemia. It is taken by mouth.

<span class="mw-page-title-main">Ginsenoside</span> Class of steroids

Ginsenosides or panaxosides are a class of natural product steroid glycosides and triterpene saponins. Compounds in this family are found almost exclusively in the plant genus Panax (ginseng), which has a long history of use in traditional medicine that has led to the study of pharmacological effects of ginseng compounds. As a class, ginsenosides exhibit a large variety of subtle and difficult-to-characterize biological effects when studied in isolation.

In enzymology, a scymnol sulfotransferase is an enzyme that catalyzes the chemical reaction

Clindamycin/tretinoin is a topical gel used in the treatment of acne. The two active ingredients are the antibiotic clindamycin phosphate (1.2%) and tretinoin (0.025%), a retinoid. The two active ingredients perform different functions, the clindamycin is active against gram-positive bacteria, including streptococci and penicillin-resistant staphylococci. The Tretinoin element acts to reduce the amount of oil released by oil glands in skin, as well as encouraging skin cell replenishment. The topical treatment is stored in 2, 30, and 60 gram tubes and should be stored at 25°C (77°F), with the tube tightly shut away from light. Side effects may include peeling, redness, dryness, itching and photosensitivity. Also, topical clindamycin may rarely cause diarrhea or colitis. Sun exposure while using this preparation can cause skin irritation.

Acne aestivalis also called as acne mallorca, is a special kind of polymorphous light eruption induced by ultra violet A radiation. This condition is said to be seasonal, usually affecting people in springtime and goes away in autumn when there is less sun light. This photo induced skin reaction leads to a mono-morphous eruption that consists of multiple, uniform, red, papular lesions. This skin reaction is classified as a delayed-type hypersensitivity because the onset is 24–72 hours after sun exposure. The condition equally affects men and women between the ages of 20–40 years old with no prior history of acne vulgaris. The eruption is unusual because it spares the face but it affects the lateral aspects of the upper arms, shoulder girdle, back, and chest. This condition's pathogenesis is not very well understood but scientists believe it an unfortunate side effect that results from a strong immune response to potentially cancer-causing cell damage.

<span class="mw-page-title-main">3-Indolepropionic acid</span> Chemical compound

3-Indolepropionic acid (IPA), or indole-3-propionic acid, has been studied for its therapeutic therapeutic value in the treatment of Alzheimer's disease. As of 2022 IPA shows potential in the treatment of this disease, though the therapeutic effect of IPA depends on dose and time of therapy initiation.

References

  1. "INCI". Personal Care Products Council.
  2. "SODIUM SCYMNOL SULFATE - Ingrédient INCI Beauty". incibeauty.com. Retrieved 2022-05-30.
  3. Dunlop, K.J.; Barnetson, R.S. (February 1995). "A comparative study of isolutrol versus benzoyl peroxide in the treatment of acne". The Australasian Journal of Dermatology. 36 (1): 13–15. doi:10.1111/j.1440-0960.1995.tb00917.x. ISSN   0004-8380. PMID   7763215. S2CID   23139723.
  4. 1 2 Chaston, Ian (2017-01-28). Technological Entrepreneurship: Technology-Driven vs Market-Driven Innovation. Springer. ISBN   978-3-319-45850-2.
  5. 1 2 Macrides et al, A comparison of the hydroxyl radical scavenging properties of the shark bile steroid 5β-scymnol and plant pycnogenols, Biochem Mol Biol Int. 1997 Sep;42(6):1249-60
  6. Kosuge, Y., Kosuge, T., Tsuji, K., Ishida, H., and Broadbent, J. M. (1989). Scymnol sulphate salts isolated from shark tissues for the treatment of liver and skin ailments (Patent: PCTInt Appl. WO 8801274-C.I. CO7J31/ 00). Chem. Abslr. 110, 88640g
  7. Muthusamy, Visalini; Hodges, Lynn D.; Macrides, Theodore A.; Boyle, Glen M.; Piva, Terrence J. (2011). "Effect of Novel Marine Nutraceuticals on IL-1α-Mediated TNF-α Release from UVB-Irradiated Human Melanocyte-Derived Cells". Oxidative Medicine and Cellular Longevity. 2011: 728645. doi: 10.1155/2011/728645 . ISSN   1942-0900. PMC   3179886 . PMID   21961050.
  8. 1 2 Guardiola-Griffiths, Cristina (2011-09-01). "Medieval mean girls: on sexual rivalry and the uses of cosmetics in La Celestina". EHumanista. 19: 172–193.
  9. Zasloff, M.; Adams, A. P.; Beckerman, B.; Campbell, A.; Han, Z.; Luijten, E.; Meza, I.; Julander, J.; Mishra, A.; Qu, W.; Taylor, J. M.; Weaver, S. C.; Wong, G. C. (2011). "Squalamine as a broad-spectrum systemic antiviral agent with therapeutic potential". Proceedings of the National Academy of Sciences of the United States of America. 108 (38): 15978–15983. Bibcode:2011PNAS..10815978Z. doi: 10.1073/pnas.1108558108 . PMC   3179074 . PMID   21930925.