Zeorin

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

MedKoo CAT#: 571051

CAS#: 22570-53-2

Description: Zeorin is a hopane-type triterpene naturally occurring in lichens. It may have anti-diabetic and/or anti-tumor properties.


Price and Availability

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Zeorin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 571051
Name: Zeorin
CAS#: 22570-53-2
Chemical Formula: C30H52O2
Exact Mass: 444.3967
Molecular Weight: 444.74
Elemental Analysis: C, 81.02; H, 11.79; O, 7.19


Synonym: Zeorin

IUPAC/Chemical Name: (3S,3aS,5aR,5bS,7S,7aS,11aR,11bR,13aR,13bS)-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysen-7-ol

InChi Key: KYBLAIAGFNCVHL-PMVHANJISA-N

InChi Code: 1S/C30H52O2/c1-25(2)14-9-15-28(6)23-11-10-22-27(5)16-12-19(26(3,4)32)20(27)13-17-29(22,7)30(23,8)18-21(31)24(25)28/h19-24,31-32H,9-18H2,1-8H3/t19-,20-,21-,22+,23+,24-,27-,28+,29+,30+/m0/s1

SMILES Code: C1[C@@]2([C@@H]([C@@]3([C@@H](C1)[C@H](CC3)C(O)(C)C)C)CC[C@H]1[C@@]2(C[C@@H]([C@@H]2[C@@]1(CCCC2(C)C)C)O)C)C


Technical Data

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:
>2 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).

Harmonized System Code:
293490


References

1: Isaka M, Sappan M, Jennifer Luangsa-Ard J, Hywel-Jones NL, Mongkolsamrit S, Chunhametha S. Chemical taxonomy of Torrubiella s. lat.: zeorin as a marker of Conoideocrella. Fungal Biol. 2011 Apr-May;115(4-5):401-5. doi: 10.1016/j.funbio.2011.02.007. Epub 2011 Feb 17. PubMed PMID: 21530922.

2: Yosioka I, Yamaki M, Kitagawa I. On the triterpenic constituents of a lichen, Parmelia entotheiochroa Hue.; zeorin, leucotylin, leucotylic acid, and five new related triterpenoids. Chem Pharm Bull (Tokyo). 1966 Jul;14(7):804-7. PubMed PMID: 5967162.

3: Shibata S, Furuya T, Iizuka H. Gas-liquid chromatography of lichen substances. I. Studies on zeorin. Chem Pharm Bull (Tokyo). 1965 Oct;13(10):1254-7. PubMed PMID: 5864709.

4: Tsuda Y, Isobe K, Fukushima S, Ageta H, Iwata K. Final clarification of the saturated hydrocarbons derived from hydroxyhopanone, diploptene, zeorin, and dustanin. Tetrahedron Lett. 1967 Jan;1:23-8. PubMed PMID: 6044785.

5: Wang ZB, Guo JT, Yang CJ, Meng YH, Wang QH, Yang BY, Kuang HX. [Chemical constituents from Hydrangea macrophylla]. Zhongguo Zhong Yao Za Zhi. 2013 Mar;38(5):709-13. Chinese. PubMed PMID: 23724681.

6: Isaka M, Hywel-Jones NL, Sappan M, Mongkolsamrit S, Saidaengkham S. Hopane triterpenes as chemotaxonomic markers for the scale insect pathogens Hypocrella s. lat. and Aschersonia. Mycol Res. 2009 Apr;113(Pt 4):491-7. PubMed PMID: 19422075.

7: Wong SM, Oshima Y, Pezzuto JM, Fong HH, Farnsworth NR. Plant anticancer agents XXXIX: Triterpenes from Iris missouriensis (Iridaceae). J Pharm Sci. 1986 Mar;75(3):317-20. PubMed PMID: 3701620.

8: Thadhani VM, Karunaratne V. Potential of Lichen Compounds as Antidiabetic Agents with Antioxidative Properties: A Review. Oxid Med Cell Longev. 2017;2017:2079697. doi: 10.1155/2017/2079697. Epub 2017 Apr 12. Review. PubMed PMID: 28491237; PubMed Central PMCID: PMC5405387.

9: Isaka M, Palasarn S, Kocharin K, Hywel-Jones NL. Comparison of the bioactive secondary metabolites from the scale insect pathogens, Anamorph Paecilomyces cinnamomeus, and Teleomorph Torrubiella luteorostrata. J Antibiot (Tokyo). 2007 Sep;60(9):577-81. PubMed PMID: 17917241.

10: Wei XL, Han KS, Lee YM, Koh YJ, Hur JS. New Record of Lecanora muralis (Lichenized Fungus) in South Korea. Mycobiology. 2007 Jun;35(2):45-6. doi: 10.4489/MYCO.2007.35.2.045. Epub 2007 Jun 30. PubMed PMID: 24015068; PubMed Central PMCID: PMC3763126.

11: Bardón A, Mitre GB, Kamiya N, Toyota M, Asakawa Y. Eremophilanolides and other constituents from the Argentine liverwort Frullania brasiliensis. Phytochemistry. 2002 Jan;59(2):205-13. PubMed PMID: 11809457.

12: Wang XY, Hur H, Lee YM, Koh YJ, Hur JS. First Report of Heterodermia squamulosa (Lichenized Ascomycota, Physciaceae) in South Korea. Mycobiology. 2008 Sep;36(3):190-2. doi: 10.4489/MYCO.2008.36.3.190. Epub 2008 Sep 30. PubMed PMID: 23997623; PubMed Central PMCID: PMC3755192.

13: Nugroho AE, Agistia DD, Tegar M, Purnomo H. Interaction of active compounds from Aegle marmelos CORREA with histamine-1 receptor. Bioinformation. 2013 Apr 30;9(8):383-7. doi: 10.6026/97320630009383. Print 2013. PubMed PMID: 23750086; PubMed Central PMCID: PMC3670119.

14: Yoshioka I, Nakanishi T, Kitagawa I. The chemical prooff of hopane skeleton of zeorin. Chem Pharm Bull (Tokyo). 1967 Mar;15(3):353-5. PubMed PMID: 6075493.

15: Feng J, Yang X, Su S, He C. [Studies on chemical constituents from herbs of Usnea longissima]. Zhongguo Zhong Yao Za Zhi. 2009 Mar;34(6):708-11. Chinese. PubMed PMID: 19624010.

16: Enzien M, Margulis L. Niebla ceruchis from Laguna Figueroa: dimorphic spore morphology and secondary compounds localized in pycnidia and apothecia. Microbios. 1988;55:75-83. PubMed PMID: 11542138.