12771-68-5

Basic information

• Product Name: Ancymidol
• Synonyms: CYCLOPROPYL(4-METHOXYPHENYL)-5-PYRIMIDYLMETHANOL;A-REST;A-REST(R);A-CYCLOPROPYL-A(P-METHOXYPHENYL)-5-PYRIMIDINE METHANOL;ALPHA-CYCLOPROPYL-ALPHA-[4-METHOXYPHENYL]-5-PYRIMIDINE-METHANOL;alpha-cyclopropyl-alpha-(4-methoxyphenyl)-5-pyrimidylmethanol;ALPHA-CYCLOPROPYL-ALPHA(P-METHOXYPHENYL)-5-PYRIMIDINE METHANOL;ANCYMIDOL
• CAS NO: 12771-68-5
• Molecular Formula: C₁₅H₁₆N₂O₂
• Molecular Weight: 256.3
• EINECS: 235-814-7
• Product Categories: plantgrowth
• Mol File: 12771-68-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 110-111°C
• Boiling Point: 399.55°C (rough estimate)
• Flash Point: 221.225 °C
• Appearance: /
• Density: 1.1055 (rough estimate)
• Vapor Pressure: 1.35E-08mmHg at 25°C
• Refractive Index: 1.6280 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.62±0.29(Predicted)
• Water Solubility: 0.65g/L(25 oC)
• CAS DataBase Reference: Ancymidol(CAS DataBase Reference)
• NIST Chemistry Reference: Ancymidol(12771-68-5)
• EPA Substance Registry System: Ancymidol(12771-68-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: UV9280000
• Hazardous Substances Data: 12771-68-5(Hazardous Substances Data)

Usage

Chemical Properties

Ancymidol is a white to buff colored crystalline or granular solid. Slightly aromatic odor.

Uses

Different sources of media describe the Uses of 12771-68-5 differently. You can refer to the following data:
1. Plant growth regulator.
2. Ancymidol has been used as the cytochrome P450 inhibitor to study its effects on Cyanidioschyzon merolae?strain.

Definition

ChEBI: A tertiary alcohol that is methanol in which the hydrogens attached to the carbon are replaced by cyclopropyl, p-methoxyphenyl and pyrimidin-5-yl groups. By inhibiting gibberellin biosynthesis, ancymidol reduces plant growth, resulting in redu ed internode elongation and thus more compact plants. It is used in the commercial production of a wide variety of container-grown bedding and foliage plants, including chrysanthemums, Easter lilies and poinsettias.

General Description

Ancymidol, a-cyclopropyl-a-(4-methoxyphenyl)-5-pyrimidinemethanol (EL-53 1), a plant growth retardant is a synthetic pyrimidine analogue. It is also a weak fungitoxic.

Biochem/physiol Actions

Ancymidol is a pyrimidine-class plant cell endocrine disruptor plant growth regulator that interferes with gibberellin and cellulose biosynthesis.

Potential Exposure

Ancymidol is a plant growth regulator registered for treating container-grown herbaceous plants, ornamental woody shrubs, and bedding plants grown in greenhouses and other plant bedding areas for primarily commercial production. Growth regulator used on plants such as chrysanthemums, certain lilies, and poinsettias effects produced by ancymidol are the result of inhibition of gibberellin biosynthesis. It produces a more compact growth form by suppressing elongation.

Incompatibilities

Dust may form explosive mixture with air. Ancymidol may react vigorously with oxidizing agents. Mixtures with concentrated hydrogen peroxide or strong mineral acids (e.g., nitric, sulfuric, perchloric) may cause explosions. Mixtures with hypochlorous acid, lead perchlorate, chlorine, bleaches, including sodium hypochlorite; mixed water/carbon tetrachloride solution; trichloroisocyanuric acid form methyl hypochlorite, which can be explosive, especially when exposed to sunlight or heat. May react with metallic aluminum at high temperature. Flow or agitation of substance may generate electrostatic charges due to low conductivity; ground all equipment containing this material. May attacks some plastics, rubber, and coatings.

Waste Disposal

Dispose of contents and container to an approved waste disposal plant. All federal, state, and local environmental regulations must be observed. References

InChI:InChI=1/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

Synthetic route

5-bromopyrimidine (4595-59-9) + p-methoxyphenyl cyclopropyl ketone (7152-03-6) → ancymidole (12771-68-5)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -95 - 20℃;	43%

4-(methoxybenzyl)-5-pyrimidyl ketone (1187168-54-2) + cyclopropylmagnesium bromide (23719-80-4) → ancymidole (12771-68-5)

Conditions	Yield
With lithium chloride; zinc(II) chloride In tetrahydrofuran at 20℃; for 4h;	31%

p-methoxybenzyl chloride (824-94-2) → ancymidole (12771-68-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: zinc; iodine; lithium chloride / ethylene dibromide / tetrahydrofuran / 6 h / 20 °C / Reflux 1.2: 0.17 h / 20 °C 2.1: potassium permanganate / ethyl acetate; water / 12 h / 20 °C 3.1: lithium chloride; zinc(II) chloride / tetrahydrofuran / 4 h / 20 °C View Scheme

4-(methoxybenzyl)pyrimidine (494228-63-6) → ancymidole (12771-68-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium permanganate / ethyl acetate; water / 12 h / 20 °C 2: lithium chloride; zinc(II) chloride / tetrahydrofuran / 4 h / 20 °C View Scheme

ancymidole (12771-68-5) → (+)-ancymidol + (-)-ancymidol

Conditions	Yield
With Lux Cellulose-2 (cellulose tris-(3-chloro-4-methylphenylcarbamate) In hexane; isopropyl alcohol at 20℃; Thermodynamic data; Reagent/catalyst; Temperature; Resolution of racemate;

Upstream product

• 494228-63-6 4-(methoxybenzyl)pyrimidine 
• 824-94-2 p-methoxybenzyl chloride 
• 1187168-54-2 4-(methoxybenzyl)-5-pyrimidyl ketone 
• 23719-80-4 cyclopropylmagnesium bromide 
• 4595-59-9 5-bromopyrimidine 
• 7152-03-6 p-methoxyphenyl cyclopropyl ketone 

Related news

Cytokinins and Ancymidol (cas 12771-68-5) inhibit Abscisic Acid Biosynthesis in Persea gratissima08/31/2019

SummaryThe cytokinins, benzyl adenine, kinetin, isopentenyl adenine, and zeatin and the cytokinin analogue, ancymidol all inhibited the biosynthesis of abscisic acid from mevalonic acid in mesocarp tissue from ripe fruits of avocado (Persea gratissima).detailed

Poinsettia response to pre-plant rooting-cube application of Ancymidol (cas 12771-68-5) and chlormequat08/29/2019

Rooted cuttings of poinsettia (Euphorbia pulcherrima Willd.) propagated in Oasis® Rootcubes® were pre-treated by direct application of ancymidol (α-cyclopropyl-α-(4-methoxyphenyl)-5-pyrimidinemethanol) or chlormequat (2-chloroethyl-trimethylammonium chloride) to cubes prior to planting. Soil d...detailed

Effect of planting-date and application method on Ancymidol (cas 12771-68-5) response of hybrid lilies08/28/2019

Ancymidol [α-cyclopropyl-α-(4-methoxyphenyl)-5-pyrimidinemethanol] was applied to commercially pre-cooled bulbs of Lilium cultivar ‘Gold Nugget’ at 0, 0.25, 0.5 or 1 mg per bulb as a bulb dip prior to planting, as a soil drench at planting or at shoot emergence of 2–3 cm. Bulb dips resulted...detailed

Effect of Ancymidol (cas 12771-68-5) in combination with temperature regime, calcium nitrate, and cultivar selection on calcium deficiency symptoms during hydroponic forcing of tulip08/27/2019

Experiments were conducted to determine the effect of ancymidol, as impacted by temperature, Ca(NO3)2, and cultivar, on the prevention of Ca deficiency symptoms during hydroponic forcing of tulip (Tulipa gesneriana L.). In all treatments where tulips were forced in distilled water, Ca deficiency...detailed

Relevant articles and documents

METHOD FOR PREPARATION OF 5-SUBSTITUTED PYRIMIDINES

The present invention provides a method to prepare 5-substituted pyrimidines by reacting a 5-acylpyrimidine with a suitable nucleophile to afford a 5-methanolpyrimidine, such as flurprimidol.

Patch preparations for treating plants

The following invention introduces a patch preparation for treating plants, whereas the patch preparations comprise a chemical layer composed of at least one agrochemically active compound, at least one adhesive and optionally, one or more additives. The components are dispersed in a matrix state on a substrate which are then introduced on the roots of the plant to be treated.

Aromatase Inhibition by 5-Substituted Pyrimidines and Dihydropirimidines

The inhibition of estrogen biosynthesis has been suggested to be an effective treatment of hormone-dependent diseases, particularly breast cancer.Several series of 5-substituted pyrimidine derivatives have been synthesized and tested for their ability to inhibit the enzyme aromatase (estrogen synthetase).Compounds were evaluated in an in vitro assay that measured the inhibition of rat ovarian microsomal aromatase activity.Greatest inhibitory activity was achieved in the cases of diarylpyrimidinemethanols and diarylpyrimidinyl methanes which were substituted in the 4- and 4'-positions with electron-withdrawing substituents, particularly Cl.