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Ancymidol

Cat No.:V65491 Purity: ≥98%
Ancymidol is a biochemical compound that may be utilized as a biomaterial or organic/chemical reagent in biomedical research.
Ancymidol
Ancymidol Chemical Structure CAS No.: 12771-68-5
Product category: Biochemical Assay Reagents
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10mg
Other Sizes
Official Supplier of:
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Product Description
Ancymidol is a biochemical compound that may be utilized as a biomaterial or organic/chemical reagent in biomedical research.
Ancymidol (CAS 12771-68-5) is a pyrimidine-class plant growth regulator that interferes with gibberellin and cellulose biosynthesis. It acts as a monooxygenase inhibitor and plant cell endocrine disruptor. Ancymidol slows plant growth by inhibiting gibberellin biosynthesis, thereby reducing internode elongation and resulting in more compact plants. It is a tertiary alcohol belonging to the pyrimidine class of compounds and is used in the commercial production of container-grown bedding and foliage plants including chrysanthemums, Easter lilies, and poinsettias. The compound is available as a BioReagent for plant cell culture applications.
Biological Activity I Assay Protocols (From Reference)
Targets
Ancymidol primarily targets the gibberellin biosynthetic pathway in plants. It specifically inhibits the oxidation of ent-kaurene to ent-kaurenoic acid in the gibberellin biosynthetic pathway, leading to reduced levels of active gibberellins. The compound also interferes with cellulose biosynthesis. By reducing endogenous gibberellin levels, ancymidol restricts stem elongation, promotes more compact growth, and can influence flowering and fruit development. It acts as a cellulose synthesis inhibitor and gibberellin biosynthesis inhibitor. The compound's mode of action makes it valuable for studying gibberellin-mediated growth processes.
ln Vitro
In vitro, ancymidol has been used as a cytochrome P450 inhibitor to study its effects on Cyanidioschyzon merolae strain. The compound blocks the abnormal elongation of plant cells by inhibiting the oxidation of gibberellin biosynthetic intermediates while also suppressing plant growth by interfering with cellulose biosynthesis. It functions as a monooxygenase inhibitor. Cellular assays in plant systems typically evaluate its effects on cell elongation, gibberellin levels, and cellulose synthesis. The compound's activity is measured by assessing plant growth inhibition and morphological changes.
ln Vivo
In vivo, ancymidol is applied to plants as a growth regulator to reduce internode elongation and produce more compact plants. It is used in the commercial production of various container-grown plants including chrysanthemums, Easter lilies, and poinsettias. By reducing endogenous gibberellin levels, ancymidol restricts stem elongation and promotes more compact growth. The compound can influence flowering and fruit development. Its effects are dose-dependent and species-specific. The compound is typically applied as a foliar spray or drench in horticultural applications.
Enzyme Assay
In vitro enzyme assays for ancymidol typically evaluate its activity as a gibberellin biosynthesis inhibitor and monooxygenase inhibitor. A standard assay protocol involves incubating the compound with plant microsomal preparations or purified enzymes (e.g., ent-kaurene oxidase) in appropriate buffer systems. The compound is dissolved in DMSO and diluted to working concentrations (typically 1-100 μM). Enzyme activity is measured by quantifying the conversion of ent-kaurene to ent-kaurenoic acid using HPLC or GC-MS. IC₅₀ values are calculated from dose-response curves. The compound's ability to inhibit cellulose synthesis can also be evaluated using similar enzyme assays.
Cell Assay
Cellular assays for ancymidol typically evaluate its effects on plant cell elongation and growth. A standard protocol involves culturing plant cells or tissues (e.g., Arabidopsis seedlings, tobacco BY-2 cells) in growth medium supplemented with ancymidol at concentrations ranging from 0.1-100 μM. Cultures are maintained at appropriate temperature (typically 25°C) with a 16-hour light/8-hour dark photoperiod. Cell elongation is measured by microscopic analysis of cell length. Gibberellin levels are quantified using ELISA or LC-MS. The compound's effects on cellulose synthesis are assessed by measuring cell wall composition.
Animal Protocol
In vivo plant studies for ancymidol typically evaluate its effects on plant growth and development. A standard protocol involves growing plants (e.g., Arabidopsis, chrysanthemums, or poinsettias) in controlled environment chambers or greenhouses. Plants are treated with ancymidol via foliar spray or drench at concentrations ranging from 0.1-100 mg/L. Plant height, internode length, and flowering are monitored regularly. Gibberellin levels in plant tissues are quantified using ELISA or LC-MS. Cell wall composition and cellulose content are analyzed. The compound's effects on plant architecture and development are evaluated.
ADME/Pharmacokinetics
Pharmacokinetic data for ancymidol in animals is not applicable, as it is a plant growth regulator. The compound has a molecular weight of approximately 256.3 g/mol and is soluble in DMSO at 60 mg/mL. It is stored at room temperature. In plant systems, ancymidol is taken up through roots or foliar application and translocated to target tissues. Its persistence and metabolism in plants depend on species and environmental conditions. The compound is classified as a BioReagent for plant cell culture applications.
Toxicity/Toxicokinetics
Toxicity Data
LCLo (Rat) > 5600 mg/m³/4hr
Toxicological data for ancymidol in animals and humans is limited, as it is a plant growth regulator not intended for human use. The compound is classified for research use only. Standard safety precautions include handling with appropriate personal protective equipment (gloves, lab coat, safety goggles) in a well-ventilated area. The compound should be stored at room temperature. Acute toxicity data is not readily available in the public literature. As with all research chemicals, appropriate laboratory safety practices should be followed. No specific LD₅₀ values or detailed toxicological profiles are available in the public domain.
References

[1]. 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.

[2]. 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.

Additional Infomation
Ancymidol is a tertiary alcohol with a methanol-like structure, in which the hydrogen atoms on the carbon atoms are replaced by cyclopropyl, p-methoxyphenyl, and pyrimidin-5-yl groups. Ancymidol slows plant growth by inhibiting gibberellin biosynthesis, thereby reducing internode elongation and resulting in a more compact plant. It is widely used in the commercial production of various potted flowers and foliage plants, including chrysanthemums, Easter lilies, and poinsettias. It acts as a plant growth inhibitor, a cellulose synthesis inhibitor, and a gibberellin biosynthesis inhibitor. It is a tertiary alcohol belonging to the pyrimidine class of compounds.
Ancymidol (CAS 12771-68-5) is a pyrimidine-class plant growth regulator that interferes with gibberellin and cellulose biosynthesis. It acts as a monooxygenase inhibitor and is used in the commercial production of container-grown plants. The compound is classified as a research-use-only compound not intended for diagnostic or therapeutic purposes. It is available from multiple commercial suppliers in various pack sizes. No clinical trials or approved drug status exist for this compound as it is not a therapeutic agent. Its applications are limited to plant research and horticulture.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H16N2O2
Molecular Weight
256.30
Exact Mass
256.121
CAS #
12771-68-5
PubChem CID
25572
Appearance
White to off-white solid powder
Density
1.259 g/cm3
Boiling Point
442.2ºC at 760 mmHg
Melting Point
110-111°C
Flash Point
221.2ºC
Vapour Pressure
1.35E-08mmHg at 25°C
Index of Refraction
1.618
LogP
2.131
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
4
Heavy Atom Count
19
Complexity
295
Defined Atom Stereocenter Count
0
SMILES
COC1=CC=C(C=C1)C(C2CC2)(C3=CN=CN=C3)O
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
Chemical Name
cyclopropyl-(4-methoxyphenyl)-pyrimidin-5-ylmethanol
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 100 mg/mL (390.17 mM)
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
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

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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