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MedKoo Cat#: 130529 | Name: Trichodimerol

Description:

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

Trichodimerol is a fungal secondary metabolite. It acts as a TNF-alpha inhibitor and a selective PPARγ agonist, inhibiting TGF-β dependent cellular effects and tube formation of MDA-MB-231 cells.

Chemical Structure

Trichodimerol
Trichodimerol
CAS#145174-90-9

Theoretical Analysis

MedKoo Cat#: 130529

Name: Trichodimerol

CAS#: 145174-90-9

Chemical Formula: C28H32O8

Exact Mass: 496.2097

Molecular Weight: 496.56

Elemental Analysis: C, 67.73; H, 6.50; O, 25.78

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
Dihydrotrichodimerol
Synonym
BMS-182123, BMS182123, BMS 182123
IUPAC/Chemical Name
(1S,3R,4R,6Z,7R,8S,10R,11R,13Z,14R)-3,10-dihydroxy-6,13-bis[(2E,4E)-1-hydroxyhexa-2,4-dienylidene]-1,4,8,11-tetramethyl-2,9-dioxapentacyclo[8.4.0.03,8.04,14.07,11]tetradecane-5,12-dione
InChi Key
OFOUJHGWJJEVMF-SZJYFORJSA-N
InChi Code
InChI=1S/C28H32O8/c1-7-9-11-13-15(29)17-19-23(3)22(32)18(16(30)14-12-10-8-2)20-24(4,21(17)31)28(34)25(19,5)35-27(23,33)26(20,6)36-28/h7-14,19-20,29-30,33-34H,1-6H3/b9-7+,10-8+,13-11+,14-12+,17-15-,18-16-/t19-,20-,23-,24-,25+,26+,27-,28-/m1/s1
SMILES Code
O=C(/C([C@@]1([H])[C@]2(C)O[C@]3(O)[C@@]1(C)C/4=O)=C(O)/C=C/C=C/C)[C@]5(C)[C@@]2(O)O[C@@]3(C)[C@]5([H])C4=C(O)/C=C/C=C/C
Appearance
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 496.56 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. Liu J, Gao S, Zhou W, Chen Y, Wang Z, Zeng Z, Zhou H, Lin T. Dihydrotrichodimerol Purified from the Marine Fungus Acremonium citrinum Prevents NAFLD by Targeting PPARα. J Nat Prod. 2023 May 26;86(5):1189-1201. doi: 10.1021/acs.jnatprod.2c00990. Epub 2023 Apr 21. PMID: 37083418. 2. Schalamun M, Beier S, Hinterdobler W, Wanko N, Schinnerl J, Brecker L, Engl DE, Schmoll M. MAPkinases regulate secondary metabolism, sexual development and light dependent cellulase regulation in Trichoderma reesei. Sci Rep. 2023 Feb 2;13(1):1912. doi: 10.1038/s41598-023-28938-w. PMID: 36732590; PMCID: PMC9894936. 3. Huo XY, Lei LR, Guo WX, Hu YJ, Kuang QX, Liu MD, Peng W, Dai YF, Wang D, Gu YC, Guo DL, Deng Y. Trichodimerol inhibits inflammation through suppression of the nuclear transcription factor-kappaB/NOD-like receptor thermal protein domain associated protein 3 signaling pathway. Front Microbiol. 2022 Aug 23;13:999996. doi: 10.3389/fmicb.2022.999996. PMID: 36081795; PMCID: PMC9445571. 4. Duan C, Wang S, Huo R, Li E, Wang M, Ren J, Pan Y, Liu L, Liu G. Sorbicillinoid Derivatives with the Radical Scavenging Activities from the Marine-Derived Fungus Acremonium chrysogenum C10. J Fungi (Basel). 2022 May 20;8(5):530. doi: 10.3390/jof8050530. PMID: 35628785; PMCID: PMC9144096. 5. Ngo MT, Nguyen MV, Han JW, Park MS, Kim H, Choi GJ. In Vitro and In Vivo Antifungal Activity of Sorbicillinoids Produced by Trichoderma longibrachiatum. J Fungi (Basel). 2021 May 28;7(6):428. doi: 10.3390/jof7060428. PMID: 34071658; PMCID: PMC8229967. 6. Rehman SU, Yang LJ, Zhang YH, Wu JS, Shi T, Haider W, Shao CL, Wang CY. Sorbicillinoid Derivatives From Sponge-Derived Fungus Trichoderma reesei (HN-2016-018). Front Microbiol. 2020 Jun 23;11:1334. doi: 10.3389/fmicb.2020.01334. PMID: 32655528; PMCID: PMC7325520. 7. Hinterdobler W, Schuster A, Tisch D, Özkan E, Bazafkan H, Schinnerl J, Brecker L, Böhmdorfer S, Schmoll M. The role of PKAc1 in gene regulation and trichodimerol production in Trichoderma reesei. Fungal Biol Biotechnol. 2019 Sep 10;6:12. doi: 10.1186/s40694-019-0075-8. PMID: 31528353; PMCID: PMC6734591. 8. Peng XP, Li G, Ji LX, Li YX, Lou HX. Acrepyrone A, a new γ-pyrone derivative from an endophytic fungus, Acremonium citrinum SS-g13. Nat Prod Res. 2020 Apr;34(8):1091-1096. doi: 10.1080/14786419.2018.1548462. Epub 2019 Jan 19. PMID: 30663360. 9. Marra R, Nicoletti R, Pagano E, DellaGreca M, Salvatore MM, Borrelli F, Lombardi N, Vinale F, Woo SL, Andolfi A. Inhibitory effect of trichodermanone C, a sorbicillinoid produced by Trichoderma citrinoviride associated to the green alga Cladophora sp., on nitrite production in LPS-stimulated macrophages. Nat Prod Res. 2019 Dec;33(23):3389-3397. doi: 10.1080/14786419.2018.1479702. Epub 2018 May 31. PMID: 29848099. 10. Monroy AA, Stappler E, Schuster A, Sulyok M, Schmoll M. A CRE1- regulated cluster is responsible for light dependent production of dihydrotrichotetronin in Trichoderma reesei. PLoS One. 2017 Aug 15;12(8):e0182530. doi: 10.1371/journal.pone.0182530. PMID: 28809958; PMCID: PMC5557485. 11. Sib A, Gulder TAM. Stereoselective Total Synthesis of Bisorbicillinoid Natural Products by Enzymatic Oxidative Dearomatization/Dimerization. Angew Chem Int Ed Engl. 2017 Oct 9;56(42):12888-12891. doi: 10.1002/anie.201705976. Epub 2017 Sep 8. PMID: 28771960. 12. Yao Y, Li J, Jiang CS, Zhao XX, Miao ZH, Liu HT, Zheng P, Ya WX, Li WQ. Trichodimerol and sorbicillin induced apoptosis of HL-60 cells is mediated by reactive oxygen species. Pharmazie. 2015 Jun;70(6):394-8. PMID: 26189301. 13. Abdel-Lateff A, Fisch K, Wright AD. Trichopyrone and other constituents from the marine sponge-derived fungus Trichoderma sp. Z Naturforsch C J Biosci. 2009 Mar-Apr;64(3-4):186-92. doi: 10.1515/znc-2009-3-406. PMID: 19526710. 14. Evidente A, Andolfi A, Cimmino A, Ganassi S, Altomare C, Favilla M, De Cristofaro A, Vitagliano S, Agnese Sabatini M. Bisorbicillinoids produced by the fungus Trichoderma citrinoviride affect feeding preference of the aphid Schizaphis graminum. J Chem Ecol. 2009 May;35(5):533-41. doi: 10.1007/s10886-009-9632-6. Epub 2009 May 6. PMID: 19418099. 15. Abdel-Lateff A. Bioproduction of sorbicillin derivatives from marine Trichoderma sp. Z Naturforsch C J Biosci. 2008 Sep-Oct;63(9-10):631-5. doi: 10.1515/znc-2008-9-1002. PMID: 19040097. 16. Serwe A, Anke T, Erkel G. The fungal secondary metabolite trichodimerol inhibits TGF-β dependent cellular effects and tube formation of MDA-MB-231 cells. Invest New Drugs. 2009 Dec;27(6):491-502. doi: 10.1007/s10637-008-9201-9. Epub 2008 Nov 14. PMID: 19009233. 17. Lee D, Lee JH, Cai XF, Shin JC, Lee K, Hong YS, Lee JJ. Fungal metabolites, sorbicillinoid polyketides and their effects on the activation of peroxisome proliferator-activated receptor gamma. J Antibiot (Tokyo). 2005 Oct;58(10):615-20. doi: 10.1038/ja.2005.84. PMID: 16392676. 18. Barnes-Seeman D, Corey EJ. A two-step total synthesis of the natural pentacycle trichodimerol, a novel inhibitor of TNF-alpha production. Org Lett. 1999 Nov 4;1(9):1503-4. doi: 10.1021/ol991070h. PMID: 10825998. 19. Nicolaou KC, Simonsen KB, Vassilikogiannakis G, Baran PS, Vidali VP, Pitsinos EN, Couladouros EA. Biomimetic Explorations Towards the Bisorbicillinoids: Total Synthesis of Bisorbicillinol, Bisorbibutenolide, and Trichodimerol. Angew Chem Int Ed Engl. 1999 Dec 3;38(23):3555-3559. doi: 10.1002/(sici)1521-3773(19991203)38:23<3555::aid-anie3555>3.0.co;2-z. PMID: 10602241. 20. Warr GA, Veitch JA, Walsh AW, Hesler GA, Pirnik DM, Leet JE, Lin PF, Medina IA, McBrien KD, Forenza S, Clark JM, Lam KS. BMS-182123, a fungal metabolite that inhibits the production of TNF-alpha by macrophages and monocytes. J Antibiot (Tokyo). 1996 Mar;49(3):234-40. doi: 10.7164/antibiotics.49.234. PMID: 8626236.

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