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Ancymidol Sale

(Synonyms: 环丙嘧啶醇) 目录号 : GC48874

A plant growth regulator

Ancymidol Chemical Structure

Cas No.:12771-68-5

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产品描述

Ancymidol is a plant growth regulator.1 It inhibits oxidation of the gibberellin biosynthetic intermediates ent-kaur-16-ene, ent-kaur-16-en-19-ol, and ent-kaur-16-en-19-al, but not ent-kaur-16-en-19-oic acid, in immature M. macrocarpus seed endosperm preparations.2 Ancymidol slows shoot and root elongation of Phaseolus vulgaris when used at concentrations ranging from 0.316 to 316 µg/ml.1

1.Shive, J.B., and Sisler, H.D.Effects of ancymidol (a growth retardant) and triarimol (a fungicide) on the growth, sterols, and gibberellins of Phaseolus vulgaris (L.)Plant Physiol.57(4)640-644(1976) 2.Coolbaugh, R.C., Hirano, S.S., and West, C.A.Studies on the specificity and site of action of α-cyclopropyl-α-[p-methoxyphenyl]-5-pyrimidine methyl alcohol (ancymidol), a plant growth regulatorPlant Physiol.62(4)571-576(1978)

Chemical Properties

Cas No. 12771-68-5 SDF
别名 环丙嘧啶醇
Canonical SMILES OC(C1=CC=C(C=C1)OC)(C2CC2)C3=CN=CN=C3
分子式 C15H16N2O2 分子量 256.3
溶解度 DMF: 30 mg/ml,DMSO: 30 mg/ml,DMSO:PBS (pH 7.2) (1:7): 0.12 mg/ml,Ethanol: 1 mg/ml 储存条件 -20°C
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1 mM 3.9017 mL 19.5084 mL 39.0168 mL
5 mM 0.7803 mL 3.9017 mL 7.8034 mL
10 mM 0.3902 mL 1.9508 mL 3.9017 mL
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Research Update

Effect of Ancymidol on cell wall metabolism in growing maize cells

Planta 2018 Apr;247(4):987-999.PMID:29330614DOI:10.1007/s00425-018-2840-y.

Ancymidol inhibits the incorporation of cellulose into cell walls of maize cell cultures in a gibberellin-independent manner, impairing cell growth; the reduction in the cellulose content is compensated with xylans. Ancymidol is a plant growth retardant which impairs gibberellin biosynthesis. It has been reported to inhibit cellulose synthesis by tobacco cells, based on its cell-malforming effects. To ascertain the putative role of Ancymidol as a cellulose biosynthesis inhibitor, we conducted a biochemical study of its effect on cell growth and cell wall metabolism in maize cultured cells. Ancymidol concentrations ≤ 500 µM progressively reduced cell growth and induced globular cell shape without affecting cell viability. However, cell growth and viability were strongly reduced by Ancymidol concentrations ≥ 1.5 mM. The I50 value for the effect of Ancymidol on FW gain was 658 µM. A reversal of the inhibitory effects on cell growth was observed when 500 µM ancymidol-treated cultures were supplemented with 100 µM GA3. Ancymidol impaired the accumulation of cellulose in cell walls, as monitored by FTIR spectroscopy. Cells treated with 500 µM Ancymidol showed a ~ 60% reduction in cellulose content, with no further change as the Ancymidol concentration increased. Cellulose content was partially restored by 100 µM GA3. Radiolabeling experiments confirmed that Ancymidol reduced the incorporation of [14C]glucose into α-cellulose and this reduction was not reverted by the simultaneous application of GA3. RT-PCR analysis indicated that the cellulose biosynthesis inhibition caused by Ancymidol is not related to a downregulation of ZmCesA gene expression. Additionally, Ancymidol treatment increased the incorporation of [3H]arabinose into a hemicellulose-enriched fraction, and up-regulated ZmIRX9 and ZmIRX10L gene expression, indicating an enhancement in the biosynthesis of arabinoxylans as a compensatory response to cellulose reduction.

The effects of Ancymidol, abscisic acid, uniconazole and paclobutrazol on somatic embryogenesis of asparagus

Plant Cell Rep 1995 May;14(8):529-33.PMID:24185526DOI:10.1007/BF00232789.

The effects of Ancymidol, abscisic acid (ABA), uniconazole, and paclobutrazol on asparagus somatic embryogenesis were evaluated. Calli induced from seedlings of genotype G447 were transferred to embryo induction medium (MS plus 3% sucrose, 0.1 mg L(-1) NAA, 0.5 mg L(-1) kinetin and 3% gelrite), with different concentrations of these compounds. After 8 weeks, the recovered bipolar or globular embryos were placed on germination medium (MS plus 6% sucrose, 0.1 mg L(-1) NAA, 0.1 mg L(-1) kinetin, 0.75 mg L(-1) Ancymidol, 40 mg L(-1) adenine sulphate dihydrate, 0.17 mg L(-1) sodium phosphate monobasic and 3% gelrite) for conversion to plantlets. Inclusion of Ancymidol, ABA, uniconazole and paclobutrazol in the embryo induction medium did not affect the total number of somatic embryos produced relative to the control without these compounds. However, Ancymidol, ABA and uniconazole significantly improved embryo development by increasing the production of bipolar embryos 250-750% and decreasing that of globular embryos 8-35% relative to the control. The bipolar embryos produced with any of the four compounds in the embryo induction medium converted to plantlets at rates 700-1100% greater than the control. None of the globular embryos converted to plantlets. Ancymidol (0.75 mg L(-1)) and ABA (0.05 mg L(-1)) were the most effective treatments; 61 and 46 bipolar embryos g(-1) callus were produced, and 38% and 37% of the bipolar embryos converted to plantlets, respectively. These results indicated that Ancymidol, ABA, uniconazole and paclobutrazol significantly enhanced the production of asparagus somatic embryos and their conversion to plantlets, and Ancymidol and ABA were more effective than uniconazole and paclobutrazol.

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.PMID:30727597DOI:10.1007/s002990050338.

Interactions of varying Ancymidol concentrations with those of α-naphthaleneacetic acid (NAA) or sucrose in embryo induction medium were related to the production and development of asparagus (Asparagus officinalis L.) somatic embryos, and to the ability of these embryos to germinate. A significant sucrose×Ancymidol interaction was observed only for the production of bipolar embryos; 4% sucrose with 0.75 mg l-1 Ancymidol gave the best result, 78 g-1 callus. The frequency of globular embryos decreased as sucrose or Ancymidol concentrations increased. Sucrose concentration affected embryo germination; 3% and 4% sucrose were optimal with approximately 60% and 40% of bipolar and globular embryos germinating, respectively. Significant Ancymidol×NAA interactions were observed for the production of bipolar and globular embryos and their germination. Varying Ancymidol concentrations affected embryo production and germination in combination with 0.1 mg l-1 NAA, but not with 1.0 mg l-1 NAA. The treatment combination of 0.1 mg l-1 NAA with 0.75 mg l-1 Ancymidol produced the most bipolar embryos, 64 g-1 callus, and the greatest percentages of bipolar and globular embryos germinated, 63% and 42%, respectively.

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.PMID:16659542DOI:10.1104/pp.57.4.640.

The effect of the two substituted pyrimidines, Ancymidol (a growth retardant) and triarimol (a fungicide) on Phaseolus vulgaris was studied. Both compounds retarded shoot and root elongation as well as increases in fresh weight. Both compounds caused production of ethylene-like responses when given in high dosages or when applied shortly after germination. As growth retardation was shown to occur in the absence of net increase in sterol levels, neither Ancymidol nor triarimol apparently retards growth by inhibiting sterol synthesis.Both Ancymidol and triarimol treatment drastically reduced the amount of extractable gibberellin-like activity in beans. Ancymidol also either induced or enhanced the production of a compound which gave a negative response in the bioassay plant Oryza sativa var. Tan-ginbozu. The addition of gibberellin completely relieved the dwarfing effects of both Ancymidol and triarimol in dark-grown beans. It is concluded that Ancymidol and triarimol affect a gibberellin-induced growth response, probably by inhibiting gibberellin biosynthesis.

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.PMID:30759908DOI:10.1007/s002990000283.

Addition of the growth retardant Ancymidol to Narcissus shoots and lower inner leaf sections isolated from shoots cultured in liquid medium induced hyperhydric malformations associated with morphogenetic changes. Meristematic centers initiated on the basal proximal ends appeared over the entire surface of the hyperhydric leaf sections after 6 weeks in culture. The meristematic centers which formed clusters on the leaf sections developed later into buds. In leaf sections grown in the liquid medium lacking Ancymidol, hyperhydricity was not induced, and regeneration was not observed. Starch and protein levels and ascorbate peroxidase and catalase activities were examined in shoots and isolated leaf sections that were either hyperhydric or non-hyperhydric. In ancymidol-treated, hyperhydric leaf sections, ascorbate peroxidase and catalase activities were lower than in control, untreated leaf sections. The changes in starch and protein levels and in antioxidant enzymatic activities appeared to be related to the onset of meristematic-center initiation and further bud development on Narcissus hyperhydric leaf sections.