Orobanchol | CAS#220493-65-2 | canonical Strigolactone

MedKoo Cat#: 145527 | Name: Orobanchol

Description:

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

Orobanchol is detected in the root exudates of several plants and recognized as a prevalent Strigolactone. OROBANCHOL is the most prevalent canonical SL.

Chemical Structure

Orobanchol

CAS#220493-65-2

Theoretical Analysis

MedKoo Cat#: 145527

Name: Orobanchol

CAS#: 220493-65-2

Chemical Formula: C19H22O6

Exact Mass: 346.1400

Molecular Weight: 346.38

Elemental Analysis: C, 65.88; H, 6.40; O, 27.71

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

Orobanchol;

IUPAC/Chemical Name

(3aR,4R,8bR,E)-4-hydroxy-8,8-dimethyl-3-((((R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl)oxy)methylene)-3,3a,4,5,6,7,8,8b-octahydro-2H-indeno[1,2-b]furan-2-one

InChi Key

CDBBMEYPRMUMTR-KIKJJFSISA-N

InChi Code

1S/C19H22O6/c1-9-7-12(24-17(9)21)23-8-11-13-15(20)10-5-4-6-19(2,3)14(10)16(13)25-18(11)22/h7-8,12-13,15-16,20H,4-6H2,1-3H3/b11-8+/t12-,13-,15+,16-/m1/s1

SMILES Code

[H][C@@]12OC(=O)\C(=C\O[C@@H]3OC(=O)C(C)=C3)[C@]1([H])[C@@H](O)C4=C2C(C)(C)CCC4

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 346.38 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: Wakabayashi T, Ueno K, Sugimoto Y. Structure Elucidation and Biosynthesis of Orobanchol. Front Plant Sci. 2022 Feb 9;13:835160. doi: 10.3389/fpls.2022.835160. PMID: 35222492; PMCID: PMC8863659. 2: Wakabayashi T, Hamana M, Mori A, Akiyama R, Ueno K, Osakabe K, Osakabe Y, Suzuki H, Takikawa H, Mizutani M, Sugimoto Y. Direct conversion of carlactonoic acid to orobanchol by cytochrome P450 CYP722C in strigolactone biosynthesis. Sci Adv. 2019 Dec 18;5(12):eaax9067. doi: 10.1126/sciadv.aax9067. PMID: 32064317; PMCID: PMC6989309. 3: Wang Y, Durairaj J, Suárez Duran HG, van Velzen R, Flokova K, Liao CY, Chojnacka A, MacFarlane S, Schranz ME, Medema MH, van Dijk ADJ, Dong L, Bouwmeester HJ. The tomato cytochrome P450 CYP712G1 catalyses the double oxidation of orobanchol en route to the rhizosphere signalling strigolactone, solanacol. New Phytol. 2022 Sep;235(5):1884-1899. doi: 10.1111/nph.18272. Epub 2022 Jun 18. PMID: 35612785; PMCID: PMC9542622. 4: Tokunaga T, Hayashi H, Akiyama K. Medicaol, a strigolactone identified as a putative didehydro-orobanchol isomer, from Medicago truncatula. Phytochemistry. 2015 Mar;111:91-7. doi: 10.1016/j.phytochem.2014.12.024. Epub 2015 Jan 12. PMID: 25593009. 5: Changenet V, Macadré C, Boutet-Mercey S, Magne K, Januario M, Dalmais M, Bendahmane A, Mouille G, Dufresne M. Overexpression of a Cytochrome P450 Monooxygenase Involved in Orobanchol Biosynthesis Increases Susceptibility to Fusarium Head Blight. Front Plant Sci. 2021 Apr 1;12:662025. doi: 10.3389/fpls.2021.662025. PMID: 33868356; PMCID: PMC8048717. 6: Xie X, Kusumoto D, Takeuchi Y, Yoneyama K, Yamada Y, Yoneyama K. 2'-epi- orobanchol and solanacol, two unique strigolactones, germination stimulants for root parasitic weeds, produced by tobacco. J Agric Food Chem. 2007 Oct 3;55(20):8067-72. doi: 10.1021/jf0715121. Epub 2007 Sep 6. PMID: 17803261. 7: Ueno K, Nomura S, Muranaka S, Mizutani M, Takikawa H, Sugimoto Y. Ent-2'-epi- Orobanchol and its acetate, as germination stimulants for Striga gesnerioides seeds isolated from cowpea and red clover. J Agric Food Chem. 2011 Oct 12;59(19):10485-90. doi: 10.1021/jf2024193. Epub 2011 Sep 19. PMID: 21899364. 8: Flematti GR, Scaffidi A, Waters MT, Smith SM. Stereospecificity in strigolactone biosynthesis and perception. Planta. 2016 Jun;243(6):1361-73. doi: 10.1007/s00425-016-2523-5. Epub 2016 Apr 22. PMID: 27105887. 9: Homma M, Uchida K, Wakabayashi T, Mizutani M, Takikawa H, Sugimoto Y. 2-oxoglutarate-dependent dioxygenases and BAHD acyltransferases drive the structural diversification of orobanchol in Fabaceae plants. Front Plant Sci. 2024 Apr 18;15:1392212. doi: 10.3389/fpls.2024.1392212. PMID: 38699535; PMCID: PMC11063326. 10: Malik H, Kohlen W, Jamil M, Rutjes FP, Zwanenburg B. Aromatic A-ring analogues of orobanchol, new germination stimulants for seeds of parasitic weeds. Org Biomol Chem. 2011 Apr 7;9(7):2286-93. doi: 10.1039/c0ob00735h. Epub 2011 Feb 14. PMID: 21321762. 11: Wakabayashi T, Moriyama D, Miyamoto A, Okamura H, Shiotani N, Shimizu N, Mizutani M, Takikawa H, Sugimoto Y. Identification of novel canonical strigolactones produced by tomato. Front Plant Sci. 2022 Dec 14;13:1064378. doi: 10.3389/fpls.2022.1064378. Erratum in: Front Plant Sci. 2023 Feb 13;14:1151993. doi: 10.3389/fpls.2023.1151993. PMID: 36589093; PMCID: PMC9794758. 12: Zwanenburg B, Ćavar Zeljković S, Pospíšil T. Synthesis of strigolactones, a strategic account. Pest Manag Sci. 2016 Jan;72(1):15-29. doi: 10.1002/ps.4105. Epub 2015 Oct 7. Erratum in: Pest Manag Sci. 2016 Mar;72(3):637. doi: 10.1002/ps.4229. PMID: 26304779. 13: Yoneyama K, Yoneyama K, Takeuchi Y, Sekimoto H. Phosphorus deficiency in red clover promotes exudation of orobanchol, the signal for mycorrhizal symbionts and germination stimulant for root parasites. Planta. 2007 Mar;225(4):1031-8. doi: 10.1007/s00425-006-0410-1. PMID: 17260144. 14: Homma M, Wakabayashi T, Moriwaki Y, Shiotani N, Shigeta T, Isobe K, Okazawa A, Ohta D, Terada T, Shimizu K, Mizutani M, Takikawa H, Sugimoto Y. Insights into stereoselective ring formation in canonical strigolactone: Identification of a dirigent domain-containing enzyme catalyzing orobanchol synthesis. Proc Natl Acad Sci U S A. 2024 Jun 25;121(26):e2313683121. doi: 10.1073/pnas.2313683121. Epub 2024 Jun 21. PMID: 38905237; PMCID: PMC11214005. 15: Wu S, Ma X, Zhou A, Valenzuela A, Zhou K, Li Y. Establishment of strigolactone-producing bacterium-yeast consortium. Sci Adv. 2021 Sep 17;7(38):eabh4048. doi: 10.1126/sciadv.abh4048. Epub 2021 Sep 17. PMID: 34533983; PMCID: PMC8448452. 16: Xie X, Yoneyama K, Kisugi T, Uchida K, Ito S, Akiyama K, Hayashi H, Yokota T, Nomura T, Yoneyama K. Confirming stereochemical structures of strigolactones produced by rice and tobacco. Mol Plant. 2013 Jan;6(1):153-63. doi: 10.1093/mp/sss139. Epub 2012 Nov 30. PMID: 23204500; PMCID: PMC3548624. 17: Chen GE, Wang JY, Votta C, Braguy J, Jamil M, Kirschner GK, Fiorilli V, Berqdar L, Balakrishna A, Blilou I, Lanfranco L, Al-Babili S. Disruption of the rice 4-DEOXYOROBANCHOL HYDROXYLASE unravels specific functions of canonical strigolactones. Proc Natl Acad Sci U S A. 2023 Oct 17;120(42):e2306263120. doi: 10.1073/pnas.2306263120. Epub 2023 Oct 11. PMID: 37819983; PMCID: PMC10589652. 18: Yoneyama K, Xie X, Yoneyama K, Takeuchi Y. Strigolactones: structures and biological activities. Pest Manag Sci. 2009 May;65(5):467-70. doi: 10.1002/ps.1726. PMID: 19222028. 19: Zhang Y, Cheng X, Wang Y, Díez-Simón C, Flokova K, Bimbo A, Bouwmeester HJ, Ruyter-Spira C. The tomato MAX1 homolog, SlMAX1, is involved in the biosynthesis of tomato strigolactones from carlactone. New Phytol. 2018 Jul;219(1):297-309. doi: 10.1111/nph.15131. Epub 2018 Apr 14. PMID: 29655242. 20: Zwanenburg B, Blanco-Ania D. Strigolactones: new plant hormones in the spotlight. J Exp Bot. 2018 Apr 23;69(9):2205-2218. doi: 10.1093/jxb/erx487. PMID: 29385517.