Alisol C Monoacetate | CAS# 26575-93-9 | Triterpenoid

MedKoo Cat#: 112024 | Name: Alisol C Monoacetate

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Description:

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

Alisol C monoacetate is a triterpenoid that has been found in Alisma orientale and has diverse biological activities. It is active against certain antibiotic-resistant strains of S. aureus, E. faecium, E. coli, and P. aeruginosa (MICs = 2.5-5 µg/ml) but not against other antibiotic-resistant strains of S. aureus or E. coli (MICs = >256 µg/ml). Alisol C monoacetate (1-10 µM) inhibits osteoclast formation induced by calcitriol in a co-culture of primary rat osteoblasts and primary rat bone marrow cells. It reduces trabecular bone loss and serum levels of a variety of cytokines, including TNF-α, IL-6, and IL-1β, in an ovariectomized rat model of osteoporosis when administered at doses of 1 and 2 mg/kg. Alisol C monoacetate (10 and 50 mg/kg) also reduces ear edema in a mouse model of delayed-type hypersensitivity.

Chemical Structure

Alisol C Monoacetate

CAS# 26575-93-9

Theoretical Analysis

MedKoo Cat#: 112024

Name: Alisol C Monoacetate

CAS#: 26575-93-9

Chemical Formula: C32H48O6

Exact Mass: 528.3451

Molecular Weight: 528.73

Elemental Analysis: C, 72.69; H, 9.15; O, 18.16

Price and Availability

Size	Price	Availability
5mg	USD 350.00	2 Weeks
10mg	USD 650.00	2 Weeks
25mg	USD 1,250.00	2 Weeks

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Related CAS #

No Data

Synonym

AC23A; Alisol C 23-acetate; Alisol C 23acetate; Alisol C 23 acetate

IUPAC/Chemical Name

(1S,3R)-1-((R)-3,3-dimethyloxiran-2-yl)-3-((5R,8S,9S,10S,11S,14R)-11-hydroxy-4,4,8,10,14-pentamethyl-3,16-dioxo-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)butyl acetate

InChi Key

KOOCQNIPRJEMDH-QSKXMHMESA-N

InChi Code

InChI=1S/C32H48O6/c1-17(14-22(37-18(2)33)27-29(5,6)38-27)25-19-15-20(34)26-30(7)12-11-24(36)28(3,4)23(30)10-13-31(26,8)32(19,9)16-21(25)35/h17,20,22-23,26-27,34H,10-16H2,1-9H3/t17-,20+,22+,23+,26+,27-,30+,31+,32+/m1/s1

SMILES Code

C[C@@]12[C@]3(C)C(C[C@H](O)[C@]1([C@]4(C)[C@@]([H])(CC2)C(C(CC4)=O)(C)C)[H])=C([C@@H](C[C@H](OC(C)=O)[C@@]5(C(O5)(C)C)[H])C)C(C3)=O

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

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	DMF	1.0	1.89
	DMSO	3.0	5.67
	Ethanol	2.0	3.78

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 528.73 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.

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: Jia X, Zhu H, Li G, Lan M, Li X, Huang M, Xu W, Wu S. Anti-osteoporotic effects of alisol C 23-acetate via osteoclastogenesis inhibition. Biomed Pharmacother. 2021 May;137:111321. doi: 10.1016/j.biopha.2021.111321. Epub 2021 Jan 29. PMID: 33524783. 2: El-Baba C, Baassiri A, Kiriako G, Dia B, Fadlallah S, Moodad S, Darwiche N. Terpenoids' anti-cancer effects: focus on autophagy. Apoptosis. 2021 Oct;26(9-10):491-511. doi: 10.1007/s10495-021-01684-y. Epub 2021 Jul 16. PMID: 34269920. 3: Xu F, Lu C, Wu Q, Gu W, Chen J, Fang F, Zhao B, Du W, You M. Studies on the lipid-regulating mechanism of alisol-based compounds on lipoprotein lipase. Bioorg Chem. 2018 Oct;80:347-360. doi: 10.1016/j.bioorg.2018.07.001. Epub 2018 Jul 2. PMID: 29986183. 4: Zhan ZJ, Bian HL, Shan WG. Alisol C 23-acetate from the rhizome of Alisma orientale. Acta Crystallogr Sect E Struct Rep Online. 2008 Oct 31;64(Pt 11):o2231. doi: 10.1107/S1600536808032959. PMID: 21581085; PMCID: PMC2959672. 5: Lee JW, Kobayashi Y, Nakamichi Y, Udagawa N, Takahashi N, Im NK, Seo HJ, Jeon WB, Yonezawa T, Cha BY, Woo JT. Alisol-B, a novel phyto-steroid, suppresses the RANKL-induced osteoclast formation and prevents bone loss in mice. Biochem Pharmacol. 2010 Aug 1;80(3):352-61. doi: 10.1016/j.bcp.2010.04.014. Epub 2010 Apr 20. PMID: 20412788. 6: Xu F, Yu H, Lu C, Chen J, Gu W. The Cholesterol-Lowering Effect of Alisol Acetates Based on HMG-CoA Reductase and Its Molecular Mechanism. Evid Based Complement Alternat Med. 2016;2016:4753852. doi: 10.1155/2016/4753852. Epub 2016 Oct 30. PMID: 27872650; PMCID: PMC5107224. 7: Zhou X, Ren Q, Wang B, Fang G, Ling Y, Li X. Alisol A 24-Acetate Isolated from the Alismatis Rhizoma Improves Hepatic Lipid Deposition in Hyperlipidemic Mice by ABCA1/ABCG1 Pathway. J Nanosci Nanotechnol. 2019 Sep 1;19(9):5496-5502. doi: 10.1166/jnn.2019.16592. PMID: 30961702. 8: Zhang X, Li XY, Lin N, Zhao WL, Huang XQ, Chen Y, Huang MQ, Xu W, Wu SS. Diuretic Activity of Compatible Triterpene Components of Alismatis rhizoma. Molecules. 2017 Sep 6;22(9):1459. doi: 10.3390/molecules22091459. PMID: 28878160; PMCID: PMC6151603. 9: Fukuyama Y, Pei-Wu G, Rei W, Yamada T, Nakagawa K. 11-deoxyalisol C and alisol D: new protostane-type triterpenoids from Alisma plantago-aquatica. Planta Med. 1988 Oct;54(5):445-7. doi: 10.1055/s-2006-962495. PMID: 17265310. 10: Jia XK, Huang JF, Huang XQ, Li XY, Huang MQ, Zhu HC, Li GP, Lan ML, Yu ZW, Xu W, Wu SS. Alismatis Rhizoma Triterpenes Alleviate High-Fat Diet-Induced Insulin Resistance in Skeletal Muscle of Mice. Evid Based Complement Alternat Med. 2021 Feb 2;2021:8857687. doi: 10.1155/2021/8857687. PMID: 33623531; PMCID: PMC7875633. 11: Tai YN, Weng YH, Zhang SP, Xu W, Li XY, Lin QQ, Chu KD, Wu SS. [Determination of seven ingredients of different grades Alismatis Rhizoma by QAMS method]. Zhongguo Zhong Yao Za Zhi. 2019 Jun;44(11):2292-2307. Chinese. doi: 10.19540/j.cnki.cjcmm.20190321.205. PMID: 31359656. 12: Yoshida I, Ito C, Matsuda S, Tsuji A, Yanaka N, Yuasa K. Alisol B, a triterpene from Alismatis rhizoma (dried rhizome of Alisma orientale), inhibits melanin production in murine B16 melanoma cells. Biosci Biotechnol Biochem. 2017 Mar;81(3):534-540. doi: 10.1080/09168451.2016.1268042. Epub 2017 Jan 4. PMID: 28051915. 13: Zhou Y, Wei W, Shen J, Lu L, Lu T, Wang H, Xue X. Alisol A 24-acetate protects oxygen-glucose deprivation-induced brain microvascular endothelial cells against apoptosis through miR-92a-3p inhibition by targeting the B-cell lymphoma-2 gene. Pharm Biol. 2021 Dec;59(1):513-524. doi: 10.1080/13880209.2021.1912117. PMID: 33905668; PMCID: PMC8081307. 14: Lee JH, Kwon OS, Jin HG, Woo ER, Kim YS, Kim HP. The rhizomes of Alisma orientale and alisol derivatives inhibit allergic response and experimental atopic dermatitis. Biol Pharm Bull. 2012;35(9):1581-7. doi: 10.1248/bpb.b110689. PMID: 22975512. 15: Xu F, Lu C, Wu Q, Chen J, Gu W, Du W, You M. Study on antitumor molecular mechanism of Alisols based on p53DNA. Int J Biol Macromol. 2018 Sep;116:1163-1174. doi: 10.1016/j.ijbiomac.2018.05.158. Epub 2018 May 22. PMID: 29800662. 16: Yu Y, Li Q, Bi K, Xie P, Yang G, Chen X. A sensitive liquid chromatography- mass spectrometry method for simultaneous determination of alisol A and alisol A 24-acetate from Alisma orientale (Sam.) Juz. in rat plasma. Anal Bioanal Chem. 2011 Jan;399(3):1363-9. doi: 10.1007/s00216-010-4426-9. Epub 2010 Nov 24. PMID: 21107819. 17: Xu YH, Zhao LJ, Li Y. Alisol B acetate induces apoptosis of SGC7901 cells via mitochondrial and phosphatidylinositol 3-kinases/Akt signaling pathways. World J Gastroenterol. 2009 Jun 21;15(23):2870-7. doi: 10.3748/wjg.15.2870. PMID: 19533808; PMCID: PMC2699004. 18: Chen HW, Hsu MJ, Chien CT, Huang HC. Effect of alisol B acetate, a plant triterpene, on apoptosis in vascular smooth muscle cells and lymphocytes. Eur J Pharmacol. 2001 May 11;419(2-3):127-38. doi: 10.1016/s0014-2999(01)00983-9. PMID: 11426834. 19: Xu F, Chen J, Wu Q, Gu W, Shen Y, Lu C, Zhang Y, Liu S, Liao H. The antitumor molecular mechanism of Alisma orientalis with c-myc DNA: multi- spectroscopic analysis and molecular simulation. J Biomol Struct Dyn. 2020 Sep;38(14):4189-4209. doi: 10.1080/07391102.2019.1688687. Epub 2019 Nov 12. PMID: 31684825. 20: Shao C, Fu B, Ji N, Pan S, Zhao X, Zhang Z, Qiu Y, Wang R, Jin M, Wen K, Kong D. Alisol B 23-Acetate Inhibits IgE/Ag-Mediated Mast Cell Activation and Allergic Reaction. Int J Mol Sci. 2018 Dec 18;19(12):4092. doi: 10.3390/ijms19124092. PMID: 30567287; PMCID: PMC6320761.