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.


Chemical Structure

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Zeorin
CAS# 22570-53-2

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

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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

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).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 444.74 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

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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.