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MedKoo Cat#: 461957 | Name: Scymnol

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Scymnol is a bile alcohol that is a therapeutic nutraceutical derived from marine sources.

Chemical Structure

Scymnol
Scymnol
CAS#6785-34-8

Theoretical Analysis

MedKoo Cat#: 461957

Name: Scymnol

CAS#: 6785-34-8

Chemical Formula: C27H48O6

Exact Mass: 468.3451

Molecular Weight: 468.68

Elemental Analysis: C, 69.19; H, 10.32; O, 20.48

Price and Availability

Related CAS #
No Data
Synonym
Scymnol; 5beta-Cholestane-3alpha,7alpha,12alpha,24,26,27-hexol
IUPAC/Chemical Name
Cholestane-3,7,12,24,26,27-hexol, (3alpha,5beta,7alpha,12alpha)-
InChi Key
DIPHJTHZUWDJIK-SWGMEOGHSA-N
InChi Code
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
SMILES Code
C[C@H](CCC(O)C(CO)CO)[C@H]1CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 468.68 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Glowacki LL, Hodges LD, Wynne PM, Wright PFA, Kalafatis N, Macrides TA. LC-MSMS characterisations of scymnol and oxoscymnol biotransformations in incubation mixtures of rat liver microsomes. Biochimie. 2019 May;160:130-140. doi: 10.1016/j.biochi.2019.02.016. Epub 2019 Mar 4. PubMed PMID: 30844411. 2: Yu D, Zhang H, Lionarons DA, Boyer JL, Cai SY. Na(+)-taurocholate cotransporting polypeptide (NTCP/SLC10A1) ortholog in the marine skate Leucoraja erinacea is not a physiological bile salt transporter. Am J Physiol Regul Integr Comp Physiol. 2017 Apr 1;312(4):R477-R484. doi: 10.1152/ajpregu.00302.2016. Epub 2017 Jan 11. PubMed PMID: 28077388; PubMed Central PMCID: PMC5407083. 3: Hodges LD, Carter F, Kalafatis N, Wright PF, Macrides TA. Elucidation of the hepatoprotective moiety of 5β-scymnol that suppresses paracetamol toxicity in mice. Mol Cell Biochem. 2016 Jun;417(1-2):135-40. doi: 10.1007/s11010-016-2720-3. Epub 2016 May 27. PubMed PMID: 27234873. 4: Muthusamy V, Hodges LD, Macrides TA, Boyle GM, Piva TJ. Effect of novel marine nutraceuticals on IL-1α-mediated TNF-α release from UVB-irradiated human melanocyte-derived cells. Oxid Med Cell Longev. 2011;2011:728645. doi: 10.1155/2011/728645. Epub 2011 Sep 22. PubMed PMID: 21961050; PubMed Central PMCID: PMC3179886. 5: Glowacki LL, Hodges LD, Wynne PM, Kalafatis N, Wright PF, Macrides TA. Hydroxysteroid dehydrogenase transformations of 5β-scymnol and identification of oxoscymnol transformation products by liquid chromatography-tandem mass spectroscopy. Steroids. 2011 Jan;76(1-2):163-8. doi: 10.1016/j.steroids.2010.10.007. Epub 2010 Oct 23. PubMed PMID: 20974163. 6: Huertas M, Hagey L, Hofmann AF, Cerdà J, Canário AV, Hubbard PC. Olfactory sensitivity to bile fluid and bile salts in the European eel (Anguilla anguilla), goldfish (Carassius auratus) and Mozambique tilapia (Oreochromis mossambicus) suggests a 'broad range' sensitivity not confined to those produced by conspecifics alone. J Exp Biol. 2010 Jan 15;213(2):308-17. doi: 10.1242/jeb.033142. PubMed PMID: 20038666. 7: Ketuly KA, A Hadi AH, Ng SW. (20R,24R,25S)-3α,7α,12α,27-Tetra-acet-oxy-24,26-ep-oxy-5β-cholestane. Acta Crystallogr Sect E Struct Rep Online. 2009 Apr 10;65(Pt 5):o1026. doi: 10.1107/S160053680901188X. PubMed PMID: 21583846; PubMed Central PMCID: PMC2977710. 8: Harney DW, Macrides TA. Synthesis of an isomeric mixture (24RS,25RS) of sodium scymnol sulfate. Steroids. 2008 Apr;73(4):424-9. doi: 10.1016/j.steroids.2007.12.006. Epub 2007 Dec 15. PubMed PMID: 18255112. 9: Cai SY, Xiong L, Wray CG, Ballatori N, Boyer JL. The farnesoid X receptor FXRalpha/NR1H4 acquired ligand specificity for bile salts late in vertebrate evolution. Am J Physiol Regul Integr Comp Physiol. 2007 Sep;293(3):R1400-9. Epub 2007 Jun 13. PubMed PMID: 17567710. 10: Slitt AL, Naylor L, Hoivik J, Manautou JE, Macrides T, Cohen SD. The shark bile salt 5 beta-scymnol abates acetaminophen toxicity, but not covalent binding. Toxicology. 2004 Oct 15;203(1-3):109-21. PubMed PMID: 15363587. 11: Elferink RP, Ottenhoff R, Fricker G, Seward DJ, Ballatori N, Boyer J. Lack of biliary lipid excretion in the little skate, Raja erinacea, indicates the absence of functional Mdr2, Abcg5, and Abcg8 transporters. Am J Physiol Gastrointest Liver Physiol. 2004 May;286(5):G762-8. Epub 2003 Dec 30. PubMed PMID: 14701720. 12: Wang W, Seward DJ, Li L, Boyer JL, Ballatori N. Expression cloning of two genes that together mediate organic solute and steroid transport in the liver of a marine vertebrate. Proc Natl Acad Sci U S A. 2001 Jul 31;98(16):9431-6. Epub 2001 Jul 24. PubMed PMID: 11470901; PubMed Central PMCID: PMC55438. 13: Ballatori N, Rebbeor JF, Connolly GC, Seward DJ, Lenth BE, Henson JH, Sundaram P, Boyer JL. Bile salt excretion in skate liver is mediated by a functional analog of Bsep/Spgp, the bile salt export pump. Am J Physiol Gastrointest Liver Physiol. 2000 Jan;278(1):G57-63. PubMed PMID: 10644562. 14: Ishida H, Nakayasu H, Tsuji K. Study of the pharmacological effect of the bile salt, sodium scymnol sulfate, from Rhizoprionodon acutus. IV. Effects of naturally occurring bile alcohols, bile acids and their conjugates on lesion development and vascular endothelial cell injury in a rat peripheral arterial occlusion model. Biol Pharm Bull. 1999 Aug;22(8):828-35. PubMed PMID: 10480321. 15: Ishida H, Nakayasu H, Nukaya H, Tsuji K. Study of the pharmacological effect of the bile salt, sodium scymnol sulfate, from Rhizoprionodon acutus. III. Protective effect of scymnol against vascular endothelial cell damage in a rat peripheral arterial occlusion model. Biol Pharm Bull. 1999 Aug;22(8):822-7. PubMed PMID: 10480320. 16: Ishida H, Nakayasu H, Nukaya H, Tsuji K. Study of the pharmacological effect of the bile salt, sodium scymnol sulfate, from Rhizoprionodon acutus. II. Prophylactic effect of scymnol on lesion development in a rat peripheral arterial occlusion model. Biol Pharm Bull. 1998 Mar;21(3):240-4. PubMed PMID: 9556153. 17: Fricker G, Wössner R, Drewe J, Fricker R, Boyer JL. Enterohepatic circulation of scymnol sulfate in an elasmobranch, the little skate (Raja erinacea). Am J Physiol. 1997 Nov;273(5 Pt 1):G1023-30. doi: 10.1152/ajpgi.1997.273.5.G1023. PubMed PMID: 9374698. 18: Macrides TA, Shihata A, Kalafatis N, Wright PF. A comparison of the hydroxyl radical scavenging properties of the shark bile steroid 5 beta-scymnol and plant pycnogenols. Biochem Mol Biol Int. 1997 Sep;42(6):1249-60. PubMed PMID: 9305543. 19: Macrides TA, Naylor LM, Kalafatis N, Shihata A, Wright PF. Hepatoprotective effects of the shark bile salt 5beta-scymnol on acetaminophen-induced liver damage in mice. Fundam Appl Toxicol. 1996 Sep;33(1):31-7. PubMed PMID: 8812214. 20: Ishida H, Kinoshita S, Yamamoto N, Nukaya H, Tsuji K, Kosuge T. Study on pharmacological effect of bile salts, sodium scymnol sulfate, from Rhizoprionodon acutus. I. Effect of scymnol, chimaerol and sodium scymnol sulfate on cerebral anoxia. Chem Pharm Bull (Tokyo). 1994 Dec;42(12):2532-5. PubMed PMID: 7697769