Synonym
Kryptogenin; Cryptogenin; Cryptogenine
IUPAC/Chemical Name
3beta,26-Dihydroxycholest-5-ene-16,22-dione
InChi Key
GDKGOXUWEBGZBY-NOIOWZGKSA-N
InChi Code
InChI=1S/C27H42O4/c1-16(15-28)5-8-23(30)17(2)25-24(31)14-22-20-7-6-18-13-19(29)9-11-26(18,3)21(20)10-12-27(22,25)4/h6,16-17,19-22,25,28-29H,5,7-15H2,1-4H3/t16?,17-,19+,20-,21+,22+,25+,26+,27+/m1/s1
SMILES Code
CC(CO)CCC([C@@H](C)[C@H]1C(C[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)=O)=O
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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
430.63
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.
| 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: Alessandrini L, Ciuffreda P, Santaniello E, Terraneo G. Clemmensen reduction of diosgenin and kryptogenin: synthesis of [16,16,22,22,23,23-(2)H(6)]-(25R)-26-hydroxycholesterol. Steroids. 2004 Dec;69(13-14):789-94. PubMed PMID: 15582533.
2: KAUFMANN S, ROSENKRANZ G. Steroidal sapogenins; transformation of kryptogenin into diosgenin and pseudodiosgenin. J Am Chem Soc. 1948 Oct;70(10):3502-5. PubMed PMID: 18891907.
3: ROSENKRANZ G, KAUFMANN S, et al. Steroidal sapogenins; new derivatives of kryptogenin. J Am Chem Soc. 1948 Oct;70(10):3518-20. PubMed PMID: 18933565.
4: Smith AG, Gilbert JD, Harland WA, Brooks CJ. The isolation of cholest-5-ene-3beta,26-diol from human brain. Biochem J. 1974 Jun;139(3):793-5. PubMed PMID: 4854921; PubMed Central PMCID: PMC1166347.
5: Kessar SV, Gupta YP, Mahajan RK, Joshi GS, Rampal AL. Synthetic studies in steroidal sapogenins and alkaloids. V. Synthesis of kryptogenin, diosgenin and yamogenin. Tetrahedron. 1968 Jan;24(2):899-904. PubMed PMID: 5637491.
6: Liu Y, Zhao DM, Lu XH, Wang H, Chen H, Ke Y, Leng L, Cheng MS. Synthesis of bisdesmosidic kryptogenyl saponins using the 'random glycosylation' strategy and evaluation of their antitumor activity. Bioorg Med Chem Lett. 2007 Jan 1;17(1):156-60. Epub 2006 Oct 10. PubMed PMID: 17035008.
7: Noll BW, Doisy EA Jr, Elliott WH. Bile acids. 39. Metabolism of 5 -cholestane-3 ,26-diol and 5 -cholestane-3 ,7 ,26-triol in the rat with a bile fistula. J Lipid Res. 1973 Jul;14(4):391-9. PubMed PMID: 4715322.
8: Javitt NB, Kok E, Lloyd J, Benscath A, Field FH. Cholest-5-ene-3 beta, 26-diol: synthesis and biomedical use of a deuterated compound. Biomed Mass Spectrom. 1982 Feb;9(2):61-3. PubMed PMID: 7059660.
9: Shoda J, Axelson M, Sjövall J. Synthesis of potential C27-intermediates in bile acid biosynthesis and their deuterium-labeled analogs. Steroids. 1993 Mar;58(3):119-25. PubMed PMID: 8475516.
10: Mui MM, Kamat SY, Elliott WH. Bile acids XLII. Preparation of 5-alpha-cholestan-26-oic acids from kryptogenin. Steroids. 1974 Aug;24(2):239-50. PubMed PMID: 4472434.
11: Kessar SV, Gupta YP, Rampal AL. Synthetic studies in steroidal alkaloids and sapogenins. I. Synthesis of kryptogenin and diosgenin. Tetrahedron Lett. 1966 Sep;36:4319-23. PubMed PMID: 5925602.
