Obtusifoliol

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

MedKoo CAT#: 464763

CAS#: 16910-32-0

Description: Obtusifoliol is a natural cell growth inhibitor.


Chemical Structure

img
Obtusifoliol
CAS# 16910-32-0

Theoretical Analysis

MedKoo Cat#: 464763
Name: Obtusifoliol
CAS#: 16910-32-0
Chemical Formula: C30H50O
Exact Mass: 426.3862
Molecular Weight: 426.729
Elemental Analysis: C, 84.44; H, 11.81; O, 3.75

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Obtusifoliol;

IUPAC/Chemical Name: (3S,4S,5S,10S,13R,14R,17R)-4,10,13,14-tetramethyl-17-((R)-6-methyl-5-methyleneheptan-2-yl)-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

InChi Key: MMNYKQIDRZNIKT-VSADUBDNSA-N

InChi Code: InChI=1S/C30H50O/c1-19(2)20(3)9-10-21(4)23-13-17-30(8)26-12-11-24-22(5)27(31)15-16-28(24,6)25(26)14-18-29(23,30)7/h19,21-24,27,31H,3,9-18H2,1-2,4-8H3/t21-,22+,23-,24+,27+,28+,29-,30+/m1/s1

SMILES Code: O[C@H]1CC[C@]2(C)C3=C([C@]4(C)CC[C@H]([C@@H](CCC(C(C)C)=C)C)[C@@]4(C)CC3)CC[C@@]2([H])[C@@H]1C

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

Preparing Stock Solutions

The following data is based on the product molecular weight 426.729 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

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Jaramillo-Madrid AC, Abbriano R, Ashworth J, Fabris M, Pernice M, Ralph PJ. Overexpression of Key Sterol Pathway Enzymes in Two Model Marine Diatoms Alters Sterol Profiles in Phaeodactylum tricornutum. Pharmaceuticals (Basel). 2020 Dec 21;13(12):481. doi: 10.3390/ph13120481. PMID: 33371196; PMCID: PMC7766473.

2: Jiao Z, Xu W, Zeng X, Xu X, Zhang M, Xia K. Obtusifoliol 14α-demethylase OsCYP51G1 is involved in phytosterol synthesis and affects pollen and seed development. Biochem Biophys Res Commun. 2020 Aug 13;529(1):91-96. doi: 10.1016/j.bbrc.2020.05.216. Epub 2020 Jun 6. PMID: 32560825.

3: Yuen H, Hung A, Yang AWH, Lenon GB. Mechanisms of Action of Cassiae Semen for Weight Management: A Computational Molecular Docking Study of Serotonin Receptor 5-HT2C. Int J Mol Sci. 2020 Feb 16;21(4):1326. doi: 10.3390/ijms21041326. PMID: 32079105; PMCID: PMC7072867.

4: Hargrove TY, Wawrzak Z, Fisher PM, Child SA, Nes WD, Guengerich FP, Waterman MR, Lepesheva GI. Binding of a physiological substrate causes large-scale conformational reorganization in cytochrome P450 51. J Biol Chem. 2018 Dec 14;293(50):19344-19353. doi: 10.1074/jbc.RA118.005850. Epub 2018 Oct 16. PMID: 30327430; PMCID: PMC6302162.

5: Zhou W, Warrilow AGS, Thomas CD, Ramos E, Parker JE, Price CL, Vanderloop BH, Fisher PM, Loftis MD, Kelly DE, Kelly SL, Nes WD. Functional importance for developmental regulation of sterol biosynthesis in Acanthamoeba castellanii. Biochim Biophys Acta Mol Cell Biol Lipids. 2018 Oct;1863(10):1164-1178. doi: 10.1016/j.bbalip.2018.07.004. Epub 2018 Jul 22. PMID: 30044954; PMCID: PMC6180906.

6: Lv QZ, Qin YL, Yan L, Wang L, Zhang C, Jiang YY. NSG2 (ORF19.273) Encoding Protein Controls Sensitivity of Candida albicans to Azoles through Regulating the Synthesis of C14-Methylated Sterols. Front Microbiol. 2018 Feb 20;9:218. doi: 10.3389/fmicb.2018.00218. PMID: 29515531; PMCID: PMC5826172.

7: Parra-Lobato MC, Paredes MA, Labrador J, Saucedo-García M, Gavilanes-Ruiz M, Gomez-Jimenez MC. Localization of Sphingolipid Enriched Plasma Membrane Regions and Long-Chain Base Composition during Mature-Fruit Abscission in Olive. Front Plant Sci. 2017 Jun 29;8:1138. doi: 10.3389/fpls.2017.01138. PMID: 28706527; PMCID: PMC5489598.

8: Warrilow AGS, Parker JE, Price CL, Garvey EP, Hoekstra WJ, Schotzinger RJ, Wiederhold NP, Nes WD, Kelly DE, Kelly SL. The Tetrazole VT-1161 Is a Potent Inhibitor of Trichophyton rubrum through Its Inhibition of T. rubrum CYP51. Antimicrob Agents Chemother. 2017 Jun 27;61(7):e00333-17. doi: 10.1128/AAC.00333-17. PMID: 28483956; PMCID: PMC5487648.

9: Bailen M, Khamlichi MD, Benharref A, Martinez-Diaz RA, Gonzalez-Coloma A. New Bioactive Semisynthetic Derivatives of 31-Norlanostenol and Obtusifoliol from Euphorbia officinarum. Nat Prod Commun. 2016 Jun;11(6):733-8. PMID: 27534104.

10: Aghaei M, Yazdiniapour Z, Ghanadian M, Zolfaghari B, Lanzotti V, Mirsafaee V. Obtusifoliol related steroids from Euphorbia sogdiana with cell growth inhibitory activity and apoptotic effects on breast cancer cells (MCF-7 and MDA- MB231). Steroids. 2016 Nov;115:90-97. doi: 10.1016/j.steroids.2016.07.008. Epub 2016 Jul 26. PMID: 27474490.

11: Hargrove TY, Friggeri L, Wawrzak Z, Sivakumaran S, Yazlovitskaya EM, Hiebert SW, Guengerich FP, Waterman MR, Lepesheva GI. Human sterol 14α-demethylase as a target for anticancer chemotherapy: towards structure-aided drug design. J Lipid Res. 2016 Aug;57(8):1552-63. doi: 10.1194/jlr.M069229. Epub 2016 Jun 16. PMID: 27313059; PMCID: PMC4959870.

12: Warrilow AG, Price CL, Parker JE, Rolley NJ, Smyrniotis CJ, Hughes DD, Thoss V, Nes WD, Kelly DE, Holman TR, Kelly SL. Azole Antifungal Sensitivity of Sterol 14α-Demethylase (CYP51) and CYP5218 from Malassezia globosa. Sci Rep. 2016 Jun 13;6:27690. doi: 10.1038/srep27690. PMID: 27291783; PMCID: PMC4904373.

13: Warrilow AG, Parker JE, Price CL, Nes WD, Garvey EP, Hoekstra WJ, Schotzinger RJ, Kelly DE, Kelly SL. The Investigational Drug VT-1129 Is a Highly Potent Inhibitor of Cryptococcus Species CYP51 but Only Weakly Inhibits the Human Enzyme. Antimicrob Agents Chemother. 2016 Jul 22;60(8):4530-8. doi: 10.1128/AAC.00349-16. PMID: 27161631; PMCID: PMC4958158.

14: Gelmini F, Ruscica M, Macchi C, Bianchi V, Maffei Facino R, Beretta G, Magni P. Unsaponifiable Fraction of Unripe Fruits of Olea europaea: An Interesting Source of Anti-inflammatory Constituents. Planta Med. 2016 Feb;82(3):273-8. doi: 10.1055/s-0035-1558155. Epub 2015 Nov 6. PMID: 26544118.

15: Hargrove TY, Wawrzak Z, Lamb DC, Guengerich FP, Lepesheva GI. Structure- Functional Characterization of Cytochrome P450 Sterol 14α-Demethylase (CYP51B) from Aspergillus fumigatus and Molecular Basis for the Development of Antifungal Drugs. J Biol Chem. 2015 Sep 25;290(39):23916-34. doi: 10.1074/jbc.M115.677310. Epub 2015 Aug 12. PMID: 26269599; PMCID: PMC4583043.

16: Xia K, Ou X, Tang H, Wang R, Wu P, Jia Y, Wei X, Xu X, Kang SH, Kim SK, Zhang M. Rice microRNA osa-miR1848 targets the obtusifoliol 14α-demethylase gene OsCYP51G3 and mediates the biosynthesis of phytosterols and brassinosteroids during development and in response to stress. New Phytol. 2015 Nov;208(3):790-802. doi: 10.1111/nph.13513. Epub 2015 Jun 17. PMID: 26083975.

17: Wagatsuma T, Khan MS, Watanabe T, Maejima E, Sekimoto H, Yokota T, Nakano T, Toyomasu T, Tawaraya K, Koyama H, Uemura M, Ishikawa S, Ikka T, Ishikawa A, Kawamura T, Murakami S, Ueki N, Umetsu A, Kannari T. Higher sterol content regulated by CYP51 with concomitant lower phospholipid content in membranes is a common strategy for aluminium tolerance in several plant species. J Exp Bot. 2015 Feb;66(3):907-18. doi: 10.1093/jxb/eru455. Epub 2014 Nov 21. PMID: 25416794; PMCID: PMC4321553.

18: Warrilow AG, Hull CM, Rolley NJ, Parker JE, Nes WD, Smith SN, Kelly DE, Kelly SL. Clotrimazole as a potent agent for treating the oomycete fish pathogen Saprolegnia parasitica through inhibition of sterol 14α-demethylase (CYP51). Appl Environ Microbiol. 2014 Oct;80(19):6154-66. doi: 10.1128/AEM.01195-14. Epub 2014 Aug 1. PMID: 25085484; PMCID: PMC4178690.

19: Shamsabadipour S, Ghanadian M, Saeedi H, Rahimnejad MR, Mohammadi-Kamalabadi M, Ayatollahi SM, Salimzadeh L. Triterpenes and Steroids from Euphorbia denticulata Lam. With Anti-Herpes Symplex Virus Activity. Iran J Pharm Res. 2013 Fall;12(4):759-67. PMID: 24523756; PMCID: PMC3920720.

20: Rahier A, Karst F. Plant cyclopropylsterol-cycloisomerase: key amino acids affecting activity and substrate specificity. Biochem J. 2014 Apr 15;459(2):289-99. doi: 10.1042/BJ20131239. PMID: 24483781.