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MedKoo Cat#: 146183 | Name: Trachelogenin

Description:

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

Trachelogenin is a lignan compound primarily isolated from plants in the Veratrum and Linum genera. It has demonstrated estrogenic, anti-inflammatory, and anticancer properties, making it a candidate for hormone-related therapies and cancer treatment. Mechanistically, trachelogenin acts as a phytoestrogen, binding to estrogen receptors and modulating their activity, which can influence gene expression and cell proliferation. Its potential to interact with hormonal pathways suggests applications in managing conditions like breast cancer, osteoporosis, and menopausal symptoms.

Chemical Structure

Trachelogenin
Trachelogenin
CAS#34209-69-3

Theoretical Analysis

MedKoo Cat#: 146183

Name: Trachelogenin

CAS#: 34209-69-3

Chemical Formula: C21H24O7

Exact Mass: 388.1522

Molecular Weight: 388.42

Elemental Analysis: C, 64.94; H, 6.23; O, 28.83

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 #
No Data
Synonym
Trachelogenin;
IUPAC/Chemical Name
(3S,4S)-4-(3,4-dimethoxybenzyl)-3-hydroxy-3-(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one
InChi Key
YFVZKLQNMNKWSB-BTYIYWSLSA-N
InChi Code
1S/C21H24O7/c1-25-17-7-5-13(9-19(17)27-3)8-15-12-28-20(23)21(15,24)11-14-4-6-16(22)18(10-14)26-2/h4-7,9-10,15,22,24H,8,11-12H2,1-3H3/t15-,21-/m0/s1
SMILES Code
COC1=CC(C[C@]2(O)[C@@H](CC3=CC(OC)=C(OC)C=C3)COC2=O)=CC=C1O
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 388.42 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: Jiang T, Zhang J, Ruan B, Xi X, Yang Z, Liu J, Zhao H, Xu X, Jiang M. Trachelogenin alleviates osteoarthritis by inhibiting osteoclastogenesis and enhancing chondrocyte survival. Chin Med. 2024 Mar 1;19(1):37. doi: 10.1186/s13020-024-00909-x. PMID: 38429848; PMCID: PMC10905921. 2: Koech PK, Boldizsár I, Dobolyi A, Varró P. Effects of dibenzylbutyrolactone lignans arctigenin and trachelogenin on the motility of isolated rat ileum. Toxicol Rep. 2022 May 27;9:1222-1232. doi: 10.1016/j.toxrep.2022.05.019. PMID: 36518476; PMCID: PMC9742865. 3: Qian XJ, Jin YS, Chen HS, Xu QQ, Ren H, Zhu SY, Tang HL, Wang Y, Zhao P, Qi ZT, Zhu YZ. Trachelogenin, a novel inhibitor of hepatitis C virus entry through CD81. J Gen Virol. 2016 May;97(5):1134-1144. doi: 10.1099/jgv.0.000432. Epub 2016 Feb 15. PMID: 26879209. 4: Koech PK, Jócsák G, Boldizsár I, Moldován K, Borbély S, Világi I, Dobolyi A, Varró P. Anti-glutamatergic Effects of Three Lignan Compounds: Arctigenin, Matairesinol and Trachelogenin - An ex vivo Study on Rat Brain Slices. Planta Med. 2023 Aug;89(9):879-889. doi: 10.1055/a-2005-5497. Epub 2023 Jan 2. PMID: 36592636. 5: Shin HS, Bae MJ, Jung SY, See HJ, Kim YT, Do JR, Back SY, Choi SW, Shon DH. Enhancing Effect of Trachelogenin from Trachelospermi caulis Extract on Intestinal Barrier Function. Biol Pharm Bull. 2015;38(11):1707-13. doi: 10.1248/bpb.b15-00332. Epub 2015 Aug 11. PMID: 26268064. 6: Li L, Meng F, Guo J, Sun L, Yu N, Zhao Y. Simultaneous quantification of tracheloside and trachelogenin in rat plasma using liquid chromatography/tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 May 1;879(15-16):1033-7. doi: 10.1016/j.jchromb.2011.02.021. Epub 2011 Mar 16. PMID: 21482203. 7: Mervai Z, Sólyomváry A, Tóth G, Noszál B, Molnár-Perl I, Baghy K, Kovalszky I, Boldizsár I. Endogenous enzyme-hydrolyzed fruit of Cirsium brachycephalum: optimal source of the antiproliferative lignan trachelogenin regulating the Wnt/β-catenin signaling pathway in the SW480 colon adenocarcinoma cell line. Fitoterapia. 2015 Jan;100:19-26. doi: 10.1016/j.fitote.2014.10.017. Epub 2014 Nov 11. PMID: 25447161. 8: Moura AF, Lima KSB, Sousa TS, Marinho-Filho JDB, Pessoa C, Silveira ER, Pessoa ODL, Costa-Lotufo LV, Moraes MO, Araújo AJ. In vitro antitumor effect of a lignan isolated from Combretum fruticosum, trachelogenin, in HCT-116 human colon cancer cells. Toxicol In Vitro. 2018 Mar;47:129-136. doi: 10.1016/j.tiv.2017.11.014. Epub 2017 Nov 22. PMID: 29174024. 9: Tan XQ, Chen HS, Liu RH, Tan CH, Xu CL, Xuan WD, Zhang WD. Lignans from Trachelospermum jasminoides. Planta Med. 2005 Jan;71(1):93-5. doi: 10.1055/s-2005-837761. PMID: 15678384. 10: Boldizsár I, Kraszni M, Tóth F, Noszál B, Molnár-Perl I. Complementary fragmentation pattern analysis by gas chromatography-mass spectrometry and liquid chromatography tandem mass spectrometry confirmed the precious lignan content of Cirsium weeds. J Chromatogr A. 2010 Oct 1;1217(40):6281-9. doi: 10.1016/j.chroma.2010.08.018. Epub 2010 Aug 13. PMID: 20813375. 11: Schröder HC, Merz H, Steffen R, Müller WE, Sarin PS, Trumm S, Schulz J, Eich E. Differential in vitro anti-HIV activity of natural lignans. Z Naturforsch C J Biosci. 1990 Nov-Dec;45(11-12):1215-21. doi: 10.1515/znc-1990-11-1222. PMID: 1965681. 12: Bailly C, Thuru X. Targeting of Tetraspanin CD81 with Monoclonal Antibodies and Small Molecules to Combat Cancers and Viral Diseases. Cancers (Basel). 2023 Apr 6;15(7):2186. doi: 10.3390/cancers15072186. PMID: 37046846; PMCID: PMC10093296. 13: Sólyomváry A, Mervai Z, Molnár-Perl I, Boldizsár I. Specific hydrolysis and accumulation of antiproliferative lignans in the fruit of Leuzea carthamoides (Willd.) DC. Nat Prod Res. 2014;28(10):732-9. doi: 10.1080/14786419.2013.879473. Epub 2014 Jan 31. PMID: 24483775. 14: Moritani Y, Fukushima C, Ukita T, Miyagishima T, Ohmizu H, Iwasaki T. Stereoselective Syntheses of Cis- and Trans-Isomers of alpha-Hydroxy-alpha,beta- dibenzyl-gamma-butyrolactone Lignans: New Syntheses of (+/-)-Trachelogenin and (+/-)-Guayadequiol. J Org Chem. 1996 Oct 4;61(20):6922-6930. doi: 10.1021/jo9601932. PMID: 11667587. 15: Temml V, Kuehnl S, Schuster D, Schwaiger S, Stuppner H, Fuchs D. Interaction of Carthamus tinctorius lignan arctigenin with the binding site of tryptophan- degrading enzyme indoleamine 2,3-dioxygenase. FEBS Open Bio. 2013 Sep 7;3:450-2. doi: 10.1016/j.fob.2013.08.008. PMID: 24251110; PMCID: PMC3829989. 16: Kuehnl S, Schroecksnadel S, Temml V, Gostner JM, Schennach H, Schuster D, Schwaiger S, Rollinger JM, Fuchs D, Stuppner H. Lignans from Carthamus tinctorius suppress tryptophan breakdown via indoleamine 2,3-dioxygenase. Phytomedicine. 2013 Oct 15;20(13):1190-5. doi: 10.1016/j.phymed.2013.06.006. Epub 2013 Jul 15. PMID: 23867649; PMCID: PMC3845384. 17: Liu XT, Wang ZX, Yang Y, Wang L, Sun RF, Zhao YM, Yu NJ. Active components with inhibitory activities on IFN-γ/STAT1 and IL-6/STAT3 signaling pathways from Caulis Trachelospermi. Molecules. 2014 Aug 5;19(8):11560-71. doi: 10.3390/molecules190811560. PMID: 25100250; PMCID: PMC6270818. 18: Forgo P, Zupkó I, Molnár J, Vasas A, Dombi G, Hohmann J. Bioactivity-guided isolation of antiproliferative compounds from Centaurea jacea L. Fitoterapia. 2012 Jul;83(5):921-5. doi: 10.1016/j.fitote.2012.04.006. Epub 2012 Apr 17. PMID: 22537643. 19: Gao XL, Liao Y, Wang J, Liu XY, Zhong K, Huang YN, Gao H, Gao B, Xu ZJ. Discovery of a potent anti-yeast triterpenoid saponin, clematoside-S from Urena lobata L. Int J Mol Sci. 2015 Mar 2;16(3):4731-43. doi: 10.3390/ijms16034731. PMID: 25739085; PMCID: PMC4394445. 20: Graikou K, Kourti PM, Zengin G, Gortzi O, Danalatos N, Chinou I. Chemical Characterisation-Biological Evaluation of Greek Cultivar Cardoon Seeds (Cynara cardunculus). A By-product with Potential High Added Value. Planta Med. 2021 Oct;87(12-13):1025-1031. doi: 10.1055/a-1472-6336. Epub 2021 Apr 26. PMID: 33902129.

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