MedKoo Cat#: 112143 | Name: Isogarcinol
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Description:

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

Isogarcinol has immunosuppressant actions, inhibiting the protein phosphatase calcineurin (IC50 = 36 µM) and suppressing the proliferation of T cells.

Chemical Structure

Isogarcinol
Isogarcinol
CAS#71117-97-0

Theoretical Analysis

MedKoo Cat#: 112143

Name: Isogarcinol

CAS#: 71117-97-0

Chemical Formula: C38H50O6

Exact Mass: 602.3607

Molecular Weight: 602.81

Elemental Analysis: C, 75.71; H, 8.36; O, 15.92

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
10mg USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
Isogarcinol; Cambogin
IUPAC/Chemical Name
(3S,4aS,6R,8R)-10-(3,4-dihydroxybenzoyl)-2,2,7,7-tetramethyl-3,6,8-tris(3-methylbut-2-en-1-yl)-3,4,5,6,7,8-hexahydro-2H,9H-4a,8-methanocycloocta[b]pyran-9,11-dione
InChi Key
KXTNVBQRLRYVCO-LPSZMIQCSA-N
InChi Code
InChI=1S/C38H50O6/c1-22(2)11-14-26-20-37-21-27(15-12-23(3)4)36(9,10)44-33(37)30(31(41)25-13-16-28(39)29(40)19-25)32(42)38(34(37)43,35(26,7)8)18-17-24(5)6/h11-13,16-17,19,26-27,39-40H,14-15,18,20-21H2,1-10H3/t26-,27+,37+,38+/m1/s1
SMILES Code
CC(C)([C@](C1=O)(C2=O)C/C=C(C)\C)[C@@H](C[C@]31C[C@@H](C(C)(OC3=C2C(C4=CC(O)=C(C=C4)O)=O)C)C/C=C(C)\C)C/C=C(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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
Solvent mg/mL mM
Solubility
DMF 25.0 41.47
DMSO 25.0 41.47
Ethanol 20.0 33.18
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 602.81 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: Cen J, Shi M, Yang Y, Fu Y, Zhou H, Wang M, Su Z, Wei Q. Isogarcinol is a new immunosuppressant. PLoS One. 2013 Jun 13;8(6):e66503. doi: 10.1371/journal.pone.0066503. PMID: 23785505; PMCID: PMC3681756. 2: Li W, Li H, Zhang M, Zhong Y, Wang M, Cen J, Wu H, Yang Y, Wei Q. Isogarcinol Extracted from Garcinia mangostana L. Ameliorates Systemic Lupus Erythematosus- like Disease in a Murine Model. J Agric Food Chem. 2015 Sep 30;63(38):8452-9. doi: 10.1021/acs.jafc.5b03425. Epub 2015 Sep 22. PMID: 26330173. 3: Wang M, Xie Y, Zhong Y, Cen J, Wang L, Liu Y, Zhu Y, Tong L, Wei Q. Amelioration of Experimental Autoimmune Encephalomyelitis by Isogarcinol Extracted from Garcinia mangostana L. Mangosteen. J Agric Food Chem. 2016 Nov 30;64(47):9012-9021. doi: 10.1021/acs.jafc.6b04145. Epub 2016 Nov 16. PMID: 27933873. 4: Chen S, Han K, Li H, Cen J, Yang Y, Wu H, Wei Q. Isogarcinol Extracted from Garcinia mangostana L. Ameliorates Imiquimod-Induced Psoriasis-like Skin Lesions in Mice. J Agric Food Chem. 2017 Feb 1;65(4):846-857. doi: 10.1021/acs.jafc.6b05207. Epub 2017 Jan 24. PMID: 28081600. 5: Fu Y, Zhou H, Wang M, Cen J, Wei Q. Immune regulation and anti-inflammatory effects of isogarcinol extracted from Garcinia mangostana L. against collagen- induced arthritis. J Agric Food Chem. 2014 May 7;62(18):4127-34. doi: 10.1021/jf405790q. Epub 2014 Apr 24. PMID: 24738849. 6: Cen J, Wang M, Jiang G, Yin Y, Su Z, Tong L, luo J, Ma Y, Gao Y, Wei Q. The new immunosuppressant, isogarcinol, binds directly to its target enzyme calcineurin, unlike cyclosporin A and tacrolimus. Biochimie. 2015 Apr;111:119-24. doi: 10.1016/j.biochi.2015.02.004. Epub 2015 Feb 17. PMID: 25701551.