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

MedKoo CAT#: 534608

CAS#: 91893-83-3

Description: Garcinoic Acid is a natural and selective agonist of pregnane X receptor.


Chemical Structure

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Garcinoic Acid
CAS# 91893-83-3

Theoretical Analysis

MedKoo Cat#: 534608
Name: Garcinoic Acid
CAS#: 91893-83-3
Chemical Formula: C27H38O4
Exact Mass: 426.277
Molecular Weight: 426.597
Elemental Analysis: C, 76.02; H, 8.98; O, 15.00

Price and Availability

Size Price Availability Quantity
1.0mg USD 420.0 2 Weeks
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Synonym: Garcinoic Acid

IUPAC/Chemical Name: (2E,6E,10E)-13-[(2S)-6-Hydroxy-2,8-dimethyl-3,4-dihydrochromen-2-yl]-2,6,10-trimethyltrideca-2,6,10-trienoic acid

InChi Key: QOFWRHWADNWKSU-XRBHEKJPSA-N

InChi Code: InChI=1S/C27H38O4/c1-19(11-7-13-21(3)26(29)30)9-6-10-20(2)12-8-15-27(5)16-14-23-18-24(28)17-22(4)25(23)31-27/h9,12-13,17-18,28H,6-8,10-11,14-16H2,1-5H3,(H,29,30)/b19-9+,20-12+,21-13+/t27-/m0/s1

SMILES Code: O=C(O)/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC[C@@]1(C)CCC2=C(O1)C(C)=CC(O)=C2

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

Preparing Stock Solutions

The following data is based on the product molecular weight 426.597 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: Wallert M, Bauer J, Kluge S, Schmölz L, Chen YC, Ziegler M, Searle AK, Maxones A, Schubert M, Thürmer M, Pein H, Koeberle A, Werz O, Birringer M, Peter K, Lorkowski S. The vitamin E derivative garcinoic acid from Garcinia kola nut seeds attenuates the inflammatory response. Redox Biol. 2019 Jun;24:101166. doi: 10.1016/j.redox.2019.101166. Epub 2019 Mar 12. PMID: 30897408; PMCID: PMC6426704.

2: Alsabil K, Suor-Cherer S, Koeberle A, Viault G, Lavaud A, Temml V, Waltenberger B, Schuster D, Litaudon M, Lorkowski S, de Vaumas R, Helesbeux JJ, Guilet D, Stuppner H, Werz O, Seraphin D, Richomme P. Semisynthetic and Natural Garcinoic Acid Isoforms as New mPGES-1 Inhibitors. Planta Med. 2016 Jul;82(11-12):1110-6. doi: 10.1055/s-0042-108739. Epub 2016 Jun 10. PMID: 27286327.

3: Mazzini F, Betti M, Netscher T, Galli F, Salvadori P. Configuration of the vitamin E analogue garcinoic acid extracted from Garcinia Kola seeds. Chirality. 2009 May;21(5):519-24. doi: 10.1002/chir.20630. PMID: 18655162.

4: Popova MP, Trusheva BS, Nedialkov PT, Tsvetkova I, Pardo-Mora DP, Najdenski H, Torres-García OA, Sforcin JM, Bankova VS. New Δ-tocotrienol derivatives from Colombian propolis. Nat Prod Res. 2019 Apr 2:1-8. doi: 10.1080/14786419.2019.1590710. Epub ahead of print. PMID: 30938183.

5: Bartolini D, De Franco F, Torquato P, Marinelli R, Cerra B, Ronchetti R, Schon A, Fallarino F, De Luca A, Bellezza G, Ferri I, Sidoni A, Walton WG, Pellock SJ, Redinbo MR, Mani S, Pellicciari R, Gioiello A, Galli F. Garcinoic Acid Is a Natural and Selective Agonist of Pregnane X Receptor. J Med Chem. 2020 Apr 9;63(7):3701-3712. doi: 10.1021/acs.jmedchem.0c00012. Epub 2020 Mar 20. PMID: 32160459.

6: Terashima K, Takaya Y, Niwa M. Powerful antioxidative agents based on garcinoic acid from Garcinia kola. Bioorg Med Chem. 2002 May;10(5):1619-25. doi: 10.1016/s0968-0896(01)00428-x. PMID: 11886823.

7: Schmölz L, Wallert M, Heise J, Galli F, Werz O, Birringer M, Lorkowski S. Regulation of inflammatory pathways by an a-tocopherol long-chain metabolite and a d-tocotrienol-related natural compound. Free Radic Biol Med. 2014 Oct;75 Suppl 1:S48. doi: 10.1016/j.freeradbiomed.2014.10.813. Epub 2014 Dec 10. PMID: 26461391.

8: Okoko T. In vitro antioxidant and free radical scavenging activities of Garcinia kola seeds. Food Chem Toxicol. 2009 Oct;47(10):2620-3. doi: 10.1016/j.fct.2009.07.023. Epub 2009 Jul 25. PMID: 19635523.

9: Ville A, Viault G, Hélesbeux JJ, Guilet D, Richomme P, Séraphin D. Efficient Semi-Synthesis of Natural δ-( R)-Tocotrienols from a Renewable Vegetal Source. J Nat Prod. 2019 Jan 25;82(1):51-58. doi: 10.1021/acs.jnatprod.8b00517. Epub 2019 Jan 10. PMID: 30629440.

10: Birringer M, Lington D, Vertuani S, Manfredini S, Scharlau D, Glei M, Ristow M. Proapoptotic effects of long-chain vitamin E metabolites in HepG2 cells are mediated by oxidative stress. Free Radic Biol Med. 2010 Nov 1;49(8):1315-22. doi: 10.1016/j.freeradbiomed.2010.07.024. Epub 2010 Aug 6. PMID: 20692332.