Basic Description

Synonyms	Madecassoside\|34540-22-2\|ASIATICOSIDE A\|BNMGUJRJUUDLHW-CIZDPPTDSA-N\|MFCD03411893\|s3843\|AKOS008901372\|AC-6056\|CCG-270599\|AS-15335\|Q-100419
Specifications & Purity	98%
Shipped In	Normal

Names and Identifiers

Pubchem Sid	488201164
Pubchem Sid Url	https://pubchem.ncbi.nlm.nih.gov/substance/488201164
IUPAC Name	[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (1S,2R,4aS,6aR,6aR,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
INCHI	InChI=1S/C48H78O20/c1-19-10-11-48(13-12-46(6)22(28(48)20(19)2)8-9-27-44(4)14-24(52)39(61)45(5,18-50)38(44)23(51)15-47(27,46)7)43(62)68-42-35(59)32(56)30(54)26(66-42)17-63-40-36(60)33(57)37(25(16-49)65-40)67-41-34(58)31(55)29(53)21(3)64-41/h8,19-21,23-42,49-61H,9-18H2,1-7H3/t19-,20+,21+,23-,24-,25-,26-,27-,28+,29+,30-,31-,32+,33-,34-,35-,36-,37-,38-,39+,40-,41+,42+,44-,45+,46+,47-,48+/m1/s1
InChi Key	BNMGUJRJUUDLHW-CIZDPPTDSA-N
Canonical SMILES	CC1CCC2(CCC3(C(=CCC4C3(CC(C5C4(CC(C(C5(C)CO)O)O)C)O)C)C2C1C)C)C(=O)OC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)C)O)O)O)O)O)O)O)O
Isomeric SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C(=CC[C@H]4[C@]3(C[C@H]([C@@H]5[C@@]4(C[C@H]([C@@H]([C@@]5(C)CO)O)O)C)O)C)[C@@H]2[C@H]1C)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)O)O)O)O)O
PubChem CID	45356919
Molecular Weight	975.12

Certificates

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5 results found

Lot Number	Certificate Type	Date	Item
J2326572	Certificate of Analysis	Oct 31, 2023	M107331
D1606081	Certificate of Analysis	Aug 03, 2023	M107331
C2331524	Certificate of Analysis	Apr 12, 2023	M107331
C2331560	Certificate of Analysis	Apr 12, 2023	M107331
D2219083	Certificate of Analysis	Apr 29, 2022	M107331

References

1. Mu-Rong Liu,Ting Han,Yao Chen,Lu-Ping Qin,Han-Chen Zheng,Yao-Cheng Rui. (2004-11-13) [Effect of madecassoside on depression behavior of mice and activities of MAO in different brain regions of rats].. Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine, 2 ((6)): (440-444). [PMID:15539023]
2. Guangtao Jia,Xiuyang Lu. (2008-05-07) Enrichment and purification of madecassoside and asiaticoside from Centella asiatica extracts with macroporous resins.. Journal of chromatography. A, 1193 ((1-2)): (136-141). [PMID:18457845]
3. Marek Haftek,Sophie Mac-Mary,Marie-Aude Le Bitoux,Pierre Creidi,Sophie Seité,André Rougier,Philippe Humbert. (2008-05-28) Clinical, biometric and structural evaluation of the long-term effects of a topical treatment with ascorbic acid and madecassoside in photoaged human skin.. Experimental dermatology, 17 ((11)): (946-952). [PMID:18503551]
4. Mei Liu,Yue Dai,Xiujuan Yao,Ying Li,Yubin Luo,Yufeng Xia,Zhunan Gong. (2008-07-26) Anti-rheumatoid arthritic effect of madecassoside on type II collagen-induced arthritis in mice.. International immunopharmacology, 8 ((11)): (1561-1566). [PMID:18652917]
5. Mingzhe Gao,Xiaoyan Yuan,Hongbin Xiao. (2008-08-30) [Preparation of asiaticoside and madecassoside from the extract of Centella asiatica (L.) Urb using preparative high performance liquid chromatography].. Se pu = Chinese journal of chromatography, 26 ((3)): (362-365). [PMID:18724677]
6. Joana Gomes,Teresa Pereira,Catarina Vilarinho,Maria da Luz Duarte,Celeste Brito. (2010-02-09) Contact dermatitis due to Centella asiatica.. Contact dermatitis, 62 ((1)): (54-55). [PMID:20136880]
7. T Winitthana,N Niwattisaiwong,C Patarapanich,M H Tantisira,S Lawanprasert. (2011-02-26) In vitro inhibitory effects of asiaticoside and madecassoside on human cytochrome P450.. Toxicology in vitro : an international journal published in association with BIBRA, 25 ((4)): (890-896). [PMID:21349323]
8. Difei Bian,Mei Liu,Ying Li,Yufeng Xia,Zhunan Gong,Yue Dai. (2012-07-26) Madecassoside, a triterpenoid saponin isolated from Centella asiatica herbs, protects endothelial cells against oxidative stress.. Journal of biochemical and molecular toxicology, 26 ((10)): (399-406). [PMID:22829481]
9. P Puttarak,P Panichayupakaranant. (2012-09-13) Factors affecting the content of pentacyclic triterpenes in Centella asiatica raw materials.. Pharmaceutical biology, 50 ((12)): (1508-1512). [PMID:22966846]
10. Xueqing Shen,Miaomiao Guo,Haiyuan Yu,Dan Liu,Zhi Lu,Yanhua Lu. (2018-11-20) Propionibacterium acnes related anti-inflammation and skin hydration activities of madecassoside, a pentacyclic triterpene saponin from Centella asiatica.. Bioscience, biotechnology, and biochemistry, 83 ((3)): (561-568). [PMID:30452312]
11. Komal Rani,Mitali Tyagi,Mohit Mazumder,Akanksha Singh,Annaian Shanmugam,Krishna Dalal,Manoj Pillai,Gourinath Samudrala,Saroj Kumar,Alagiri Srinivasan. (2020-03-15) Accelerated identification of serine racemase inhibitor from Centella asiatica.. Scientific reports, 10 ((1)): (4640-4640). [PMID:32170206]
12. F Bonté,M Dumas,C Chaudagne,A Meybeck. (1995-01-01) [Comparative activity of asiaticoside and madecassoside on type I and III collagen synthesis by cultured human fibroblasts].. Annales pharmaceutiques francaises, 53 ((1)): (38-42). [PMID:7741425]
13. J H Sampson,A Raman,G Karlsen,H Navsaria,I M Leigh. (2001-06-22) In vitro keratinocyte antiproliferant effect of Centella asiatica extract and triterpenoid saponins.. Phytomedicine : international journal of phytotherapy and phytopharmacology, 8 ((3)): (230-235). [PMID:11417919]
14. Mercè Bonfill,Susana Mangas,Rosa M Cusidó,Lidia Osuna,M Teresa Piñol,Javier Palazón. (2005-10-06) Identification of triterpenoid compounds of Centella asiatica by thin-layer chromatography and mass spectrometry.. Biomedical chromatography : BMC, 20 ((2)): (151-153). [PMID:16206136]
15. Feng-Lun Zhang,Ying-Jie Wei,Jia Zhu,Zhu-Nan Gong. (2007-08-19) Simultaneous quantitation of three major triterpenoid glycosides in Centella asiatica extracts by high performance liquid chromatography with evaporative light scattering detection.. Biomedical chromatography : BMC, 22 ((2)): (119-124). [PMID:17703474]
16. Gui-Gui Li,Guang-Xing Bian,Jian-Ping Ren,Li-Qing Wen,Min Zhang,Qiu-Jun Lü. (2007-08-21) [Protective effect of madecassoside against reperfusion injury after regional ischemia in rabbit heart in vivo].. Yao xue xue bao = Acta pharmaceutica Sinica, 42 ((5)): (475-480). [PMID:17703767]
17. Guang-Xing Bian,Gui-Gui Li,Yun Yang,Rui-Ting Liu,Jian-Ping Ren,Li-Qing Wen,Shao-Ming Guo,Qiu-Jun Lu. (2008-03-04) Madecassoside reduces ischemia-reperfusion injury on regional ischemia induced heart infarction in rat.. Biological & pharmaceutical bulletin, 31 ((3)): (458-463). [PMID:18310910]
18. Mei Liu,Yue Dai,Ying Li,Yubin Luo,Fang Huang,Zhunan Gong,Qingyu Meng. (2008-05-20) Madecassoside isolated from Centella asiatica herbs facilitates burn wound healing in mice.. Planta medica, 74 ((8)): (809-815). [PMID:18484522]
19. Ok Tae Kim,Sun Hee Kim,Kiyoshi Ohyama,Toshiya Muranaka,Yong Eui Choi,Hyeon Yong Lee,Min Young Kim,Baik Hwang. (2010-03-03) Upregulation of phytosterol and triterpene biosynthesis in Centella asiatica hairy roots overexpressed ginseng farnesyl diphosphate synthase.. Plant cell reports, 29 ((4)): (403-411). [PMID:20195611]
20. Wen-Jing Han,Yu-Feng Xia,Yue Dai. (2011-03-18) Development and validation of high-performance liquid chromatography/electrospray ionization mass spectrometry for assay of madecassoside in rat plasma and its application to pharmacokinetic study.. Biomedical chromatography : BMC, 26 ((1)): (26-32). [PMID:21413047]
21. Jie Song,Huan Xu,Qian Lu,Zhao Xu,Difei Bian,Yufeng Xia,Zhifeng Wei,Zhunan Gong,Yue Dai. (2012-03-01) Madecassoside suppresses migration of fibroblasts from keloids: involvement of p38 kinase and PI3K signaling pathways.. Burns : journal of the International Society for Burn Injuries, 38 ((5)): (677-684). [PMID:22360962]

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Madecassoside - 98%, high purity , CAS No.34540-22-2