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MedKoo Cat#: 574560 | Name: Ancymidol
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Description:

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

Ancymidol is a synthetic plant growth retardant that inhibits gibberellin biosynthesis, leading to reduced cell elongation and overall plant height. Its primary mechanism of action involves the inhibition of ent-kaurene oxidase, a cytochrome P450-dependent monooxygenase critical in the gibberellin biosynthetic pathway. Ancymidol exhibits bioactivity by effectively controlling shoot growth in a variety of ornamental and agricultural plants without significantly affecting other hormonal pathways.

Chemical Structure

Ancymidol
Ancymidol
CAS# 12771-68-5

Theoretical Analysis

MedKoo Cat#: 574560

Name: Ancymidol

CAS#: 12771-68-5

Chemical Formula: C15H16N2O2

Exact Mass: 256.1212

Molecular Weight: 256.30

Elemental Analysis: C, 70.29; H, 6.29; N, 10.93; O, 12.48

Price and Availability

Size Price Availability Quantity
25mg USD 250.00 2 Weeks
100mg USD 650.00 2 Weeks
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Related CAS #
No Data
Synonym
Ancymidol; EL 531; EL531; EL-531;
IUPAC/Chemical Name
cyclopropyl(4-methoxyphenyl)(pyrimidin-5-yl)methanol
InChi Key
HUTDUHSNJYTCAR-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H16N2O2/c1-19-14-6-4-12(5-7-14)15(18,11-2-3-11)13-8-16-10-17-9-13/h4-11,18H,2-3H2,1H3
SMILES Code
COc1ccc(cc1)C(O)(C2CC2)c3cncnc3
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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
Solvent mg/mL mM comments
Solubility
Soluble in DMSO 0.0 100.00
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 256.30 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
1: Hernández-Altamirano JM, Largo-Gosens A, Martínez-Rubio R, Pereda D, Álvarez JM, Acebes JL, Encina A, García-Angulo P. Effect of ancymidol on cell wall metabolism in growing maize cells. Planta. 2018 Apr;247(4):987-999. doi: 10.1007/s00425-018-2840-y. Epub 2018 Jan 12. PMID: 29330614. 2: Li B, Wolyn DJ. The effects of ancymidol, abscisic acid, uniconazole and paclobutrazol on somatic embryogenesis of asparagus. Plant Cell Rep. 1995 May;14(8):529-33. doi: 10.1007/BF00232789. PMID: 24185526. 3: Li B, Wolyn DJ. Interactions of ancymidol with sucrose and α-naphthaleneacetic acid in promoting asparagus (Asparagus officinalis L.) somatic embryogenesis. Plant Cell Rep. 1997 Oct;16(12):879-883. doi: 10.1007/s002990050338. PMID: 30727597. 4: Shive JB, Sisler HD. Effects of Ancymidol (a Growth Retardant) and Triarimol (a Fungicide) on the Growth, Sterols, and Gibberellins of Phaseolus vulgaris (L.). Plant Physiol. 1976 Apr;57(4):640-4. doi: 10.1104/pp.57.4.640. PMID: 16659542; PMCID: PMC542088. 5: Hofmannová J, Schwarzerová K, Havelková L, Boríková P, Petrásek J, Opatrny Z. A novel, cellulose synthesis inhibitory action of ancymidol impairs plant cell expansion. J Exp Bot. 2008;59(14):3963-74. doi: 10.1093/jxb/ern250. Epub 2008 Oct 1. PMID: 18832186; PMCID: PMC2576644. 6: Feng XR, Wolyn DJ. Development of haploid asparagus embryos from liquid cultures of anther-derived calli is enhanced by ancymidol. Plant Cell Rep. 1993 Mar;12(5):281-5. doi: 10.1007/BF00237136. PMID: 24197158. 7: Coolbaugh RC, Hirano SS, West CA. Studies on the Specificity and Site of Action of alpha-Cyclopropyl-alpha-[p-methoxyphenyl]-5-pyrimidine Methyl Alcohol (Ancymidol), a Plant Growth Regulator. Plant Physiol. 1978 Oct;62(4):571-6. doi: 10.1104/pp.62.4.571. PMID: 16660561; PMCID: PMC1092173. 8: Burkhart LF, Meyer MM Jr. The gibberellin synthesis inhibitors, ancymidol and flurprimidol, promote in vitro rooting of white pine microshoots. Plant Cell Rep. 1991 Nov;10(9):475-6. doi: 10.1007/BF00233818. PMID: 24221855. 9: Chen J, Ziv M. The effect of ancymidol on hyperhydricity, regeneration, starch and antioxidant enzymatic activities in liquid-cultured Narcissus. Plant Cell Rep. 2001 Jan;20(1):22-27. doi: 10.1007/s002990000283. PMID: 30759908. 10: Desjardins AE, Plattner RD, Beremand MN. Ancymidol blocks trichothecene biosynthesis and leads to accumulation of trichodiene in Fusarium sporotrichioides and Gibberella pulicaris. Appl Environ Microbiol. 1987 Aug;53(8):1860-5. doi: 10.1128/aem.53.8.1860-1865.1987. PMID: 3662519; PMCID: PMC204014. 11: Thakur R, Sood A, Nagar PK, Pandey S, Sobti RC, Ahuja PS. Regulation of growth of Lilium plantlets in liquid medium by application of paclobutrazol or ancymidol, for its amenability in a bioreactor system: growth parameters. Plant Cell Rep. 2006 May;25(5):382-91. doi: 10.1007/s00299-005-0094-1. Epub 2005 Dec 20. PMID: 16369766. 12: Coolbaugh RC, Swanson DI, West CA. Comparative Effects of Ancymidol and Its Analogs on Growth of Peas and Ent-Kaurene Oxidation in Cell-Free Extracts of Immature Marah macrocarpus Endosperm. Plant Physiol. 1982 Mar;69(3):707-11. doi: 10.1104/pp.69.3.707. PMID: 16662280; PMCID: PMC426285. 13: Chai T, Yang W, Qiu J, Hou S. Direct enantioseparation of nitrogen- heterocyclic pesticides on cellulose-based chiral column by high-performance liquid chromatography. Chirality. 2015 Jan;27(1):32-8. doi: 10.1002/chir.22385. Epub 2014 Oct 20. PMID: 25331721. 14: Le Guen-Le Saos F, Hourmant A, Esnault F, Chauvin JE. In vitro bulb development in shallot (Allium cepa L. Aggregatum Group): effects of anti- gibberellins, sucrose and light. Ann Bot. 2002 Apr;89(4):419-25. doi: 10.1093/aob/mcf063. PMID: 12096802; PMCID: PMC4233876. 15: Akram M, Patt M, Kaserer T, Temml V, Waratchareeyakul W, Kratschmar DV, Haupenthal J, Hartmann RW, Odermatt A, Schuster D. Identification of the fungicide epoxiconazole by virtual screening and biological assessment as inhibitor of human 11β-hydroxylase and aldosterone synthase. J Steroid Biochem Mol Biol. 2019 Sep;192:105358. doi: 10.1016/j.jsbmb.2019.04.007. Epub 2019 Apr 6. PMID: 30965118. 16: Norman SM, Bennett RD, Poling SM, Maier VP, Nelson MD. Paclobutrazol Inhibits Abscisic Acid Biosynthesis in Cercospora rosicola. Plant Physiol. 1986 Jan;80(1):122-5. doi: 10.1104/pp.80.1.122. PMID: 16664565; PMCID: PMC1075067. 17: Lanahan MB, Ho TH. Slender barley: A constitutive gibberellin-response mutant. Planta. 1988 Jul;175(1):107-14. doi: 10.1007/BF00402887. PMID: 24221634. 18: Zocher G, Richter ME, Mueller U, Hertweck C. Structural fine-tuning of a multifunctional cytochrome P450 monooxygenase. J Am Chem Soc. 2011 Feb 23;133(7):2292-302. doi: 10.1021/ja110146z. Epub 2011 Jan 31. PMID: 21280577. 19: Lee I I, Foster KR, Morgan PW. Effect of Gibberellin Biosynthesis Inhibitors on Native Gibberellin Content, Growth and Floral Initiation in Sorghum bicolor. J Plant Growth Regul. 1998 Dec;17(4):185-195. doi: 10.1007/pl00007034. PMID: 9892741. 20: Warne TR, Hickok LG. Evidence for a gibberellin biosynthetic origin of ceratopteris antheridiogen. Plant Physiol. 1989 Feb;89(2):535-8. doi: 10.1104/pp.89.2.535. PMID: 16666578; PMCID: PMC1055877.

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