Cycloartenol | CAS#469-38-5 | triterpenoid

MedKoo Cat#: 146221 | Name: Cycloartenol

Description:

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

Cycloartenol is a triterpenoid compound that serves as a key intermediate in the biosynthesis of plant sterols, including important phytosterols like sitosterol and stigmasterol. Found in a wide range of plant species, it plays a crucial role in maintaining membrane structure and function. In terms of applications, cycloartenol is studied for its potential cholesterol-lowering, anti-inflammatory, and anticancer properties, particularly through its influence on sterol metabolism. Its mechanism involves acting as a precursor in the cyclization of squalene, leading to the formation of complex sterols that regulate cellular processes and signaling in plants.

Chemical Structure

Cycloartenol

CAS#469-38-5

Theoretical Analysis

MedKoo Cat#: 146221

Name: Cycloartenol

CAS#: 469-38-5

Chemical Formula: C30H50O

Exact Mass: 426.3862

Molecular Weight: 426.73

Elemental Analysis: C, 84.44; H, 11.81; O, 3.75

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Cycloartenol; Handianol;

IUPAC/Chemical Name

(2aR,3R,5aS,5bS,7aR,9S,11aR,12aS)-2a,5a,8,8-tetramethyl-3-((R)-6-methylhept-5-en-2-yl)tetradecahydro-1H,12H-cyclopenta[a]cyclopropa[e]phenanthren-9-ol

InChi Key

ONQRKEUAIJMULO-YBXTVTTCSA-N

InChi Code

1S/C30H50O/c1-20(2)9-8-10-21(3)22-13-15-28(7)24-12-11-23-26(4,5)25(31)14-16-29(23)19-30(24,29)18-17-27(22,28)6/h9,21-25,31H,8,10-19H2,1-7H3/t21-,22-,23+,24+,25+,27-,28+,29-,30+/m1/s1

SMILES Code

C[C@H](CCC=C(C)C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H]4[C@]5(C[C@@]35CC[C@]12C)CC[C@H](O)C4(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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 426.73 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: Wu L, Chen ZL, Su Y, Wang QH, Kuang HX. Cycloartenol triterpenoid saponins from Cimicifuga simplex (Ranunculaceae) and their biological effects. Chin J Nat Med. 2015 Feb;13(2):81-9. doi: 10.1016/S1875-5364(15)60011-5. PMID: 25769890; PMCID: PMC7130100. 2: Zhang ZL, Luo ZL, Shi HW, Zhang LX, Ma XJ. [Research advance of functional plant pharmaceutical cycloartenol about pharmacological and physiological activity]. Zhongguo Zhong Yao Za Zhi. 2017 Feb;42(3):433-437. Chinese. doi: 10.19540/j.cnki.cjcmm.20161222.066. PMID: 28952245. 3: Hou M, Wang R, Zhao S, Wang Z. Ginsenosides in Panax genus and their biosynthesis. Acta Pharm Sin B. 2021 Jul;11(7):1813-1834. doi: 10.1016/j.apsb.2020.12.017. Epub 2021 Jan 2. PMID: 34386322; PMCID: PMC8343117. 4: Guo SY, Yin Y, Lei T, Shi YH, Gao W, Zhang XN, Li J. A cycloartenol synthase from the steroidal saponin biosynthesis pathway of Paris polyphylla. J Asian Nat Prod Res. 2021 Apr;23(4):353-362. doi: 10.1080/10286020.2020.1730331. Epub 2020 Mar 6. PMID: 32138546. 5: Nair ANS, Nair RVR, Nair APR, Nair AS, Thyagarajan S, Johnson AJ, Baby S. Antidiabetes constituents, cycloartenol and 24-methylenecycloartanol, from Ficus krishnae. PLoS One. 2020 Jun 25;15(6):e0235221. doi: 10.1371/journal.pone.0235221. PMID: 32584888; PMCID: PMC7316276. 6: Warner SA, Eierman DF, Sovocool GW, Domnas AJ. Cycloartenol-derived sterol biosynthesis in the Peronosporales. Proc Natl Acad Sci U S A. 1982 Jun;79(12):3769-72. doi: 10.1073/pnas.79.12.3769. PMID: 16593196; PMCID: PMC346508. 7: Hage-Hülsmann J, Metzger S, Wewer V, Buechel F, Troost K, Thies S, Loeschcke A, Jaeger KE, Drepper T. Biosynthesis of cycloartenol by expression of plant and bacterial oxidosqualene cyclases in engineered Rhodobacter capsulatus. J Biotechnol. 2019;306S:100014. doi: 10.1016/j.btecx.2020.100014. Epub 2020 Feb 1. PMID: 34112372. 8: Duan Y, Du W, Song Z, Chen R, Xie K, Liu J, Chen D, Dai J. Functional characterization of a cycloartenol synthase and four glycosyltransferases in the biosynthesis of cycloastragenol-type astragalosides from Astragalus membranaceus. Acta Pharm Sin B. 2023 Jan;13(1):271-283. doi: 10.1016/j.apsb.2022.05.015. Epub 2022 May 20. PMID: 36815054; PMCID: PMC9939298. 9: Jin ML, Lee WM, Kim OT. Two Cycloartenol Synthases for Phytosterol Biosynthesis in Polygala tenuifolia Willd. Int J Mol Sci. 2017 Nov 15;18(11):2426. doi: 10.3390/ijms18112426. PMID: 29140303; PMCID: PMC5713394. 10: Ikeda I, Nakashima-Yoshida K, Sugano M. Effects of cycloartenol on absorption and serum levels of cholesterol in rats. J Nutr Sci Vitaminol (Tokyo). 1985 Jun;31(3):375-84. doi: 10.3177/jnsv.31.375. PMID: 4067669. 11: Niu H, Li X, Yang A, Jin Z, Wang X, Wang Q, Yu C, Wei Z, Dou C. Cycloartenol exerts anti-proliferative effects on Glioma U87 cells via induction of cell cycle arrest and p38 MAPK-mediated apoptosis. J BUON. 2018 Nov- Dec;23(6):1840-1845. PMID: 30610811. 12: Gas-Pascual E, Simonovik B, Schaller H, Bach TJ. Inhibition of Cycloartenol Synthase (CAS) Function in Tobacco BY-2 Cells. Lipids. 2015 Aug;50(8):761-72. doi: 10.1007/s11745-015-4036-6. Epub 2015 Jun 2. PMID: 26033687. 13: Godzina SM, Lovato MA, Meyer MM, Foster KA, Wilson WK, Gu W, de Hostos EL, Matsuda SP. Cloning and characterization of the Dictyostelium discoideum cycloartenol synthase cDNA. Lipids. 2000 Mar;35(3):249-55. doi: 10.1007/s11745-000-0520-3. PMID: 10783001. 14: Matsuda SP, Darr LB, Hart EA, Herrera JB, McCann KE, Meyer MM, Pang J, Schepmann HG. Steric bulk at cycloartenol synthase position 481 influences cyclization and deprotonation. Org Lett. 2000 Jul 27;2(15):2261-3. doi: 10.1021/ol006018w. PMID: 10930258. 15: Su Y, Wu L, Mu G, Wang Q, Yang B, Cheng G, Kuang H. 9,19-Cycloartenol glycoside G3 from Cimicifuga simplex regulates immune responses by modulating Th17/Treg ratio. Bioorg Med Chem. 2017 Sep 1;25(17):4917-4923. doi: 10.1016/j.bmc.2017.07.042. Epub 2017 Jul 27. PMID: 28780985. 16: Ragasa CY, Tiu F, Rideout JA. New cycloartenol esters from Ixora coccinea. Nat Prod Res. 2004 Aug;18(4):319-23. doi: 10.1080/14786410310001630519. PMID: 15214483. 17: Sakamoto K, Tabata T, Shirasaki K, Inagaki T, Nakayama S. Effects of gamma- oryzanol and cycloartenol ferulic acid ester on cholesterol diet induced hyperlipidemia in rats. Jpn J Pharmacol. 1987 Dec;45(4):559-65. doi: 10.1254/jjp.45.559. PMID: 3444123. 18: Gas-Pascual E, Berna A, Bach TJ, Schaller H. Plant oxidosqualene metabolism: cycloartenol synthase-dependent sterol biosynthesis in Nicotiana benthamiana. PLoS One. 2014 Oct 24;9(10):e109156. doi: 10.1371/journal.pone.0109156. PMID: 25343375; PMCID: PMC4208727. 19: Rees HH, Goad LJ, Goodwin TW. 2,3-oxidosqualene cycloartenol cyclase from Ochromonas malhamensis. Biochim Biophys Acta. 1969 Jun 10;176(4):892-4. PMID: 5797101. 20: Meyer MM, Xu R, Matsuda SP. Directed evolution to generate cycloartenol synthase mutants that produce lanosterol. Org Lett. 2002 Apr 18;4(8):1395-8. doi: 10.1021/ol0257225. PMID: 11950371.