Daminozide CAS 1596-84-5
Introduction：Basic information about Daminozide CAS 1596-84-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Daminozide Basic informationOverview Applications Mode of action Application methods Risk and Warning References Background
| Product Name: | Daminozide |
| Synonyms: | 4-(2,2-diMethylhydrazinyl)-4-oxobutanoic acid;Ferrostatin-1;DaMinozide 0.2;Daminozide Solution, 100ug/ml;Daminozide solution,100ppm;Daminozide≥ 99% (Assay);N-(Dimethylamino)succinamic acidButanedioic acid mono(2,2-dimethylhydrazide)B-NineDMASASuccinic acid 2,2-dimethylhydrazide;2,2-dimethylhydrazidkyselinyjantarove |
| CAS: | 1596-84-5 |
| MF: | C6H12N2O3 |
| MW: | 160.17 |
| EINECS: | 216-485-9 |
| Product Categories: | Plant Hormones;Miscellaneous;PLANT GROWTH REGULATOR;Pesticide intermediates |
| Mol File: | 1596-84-5.mol |
Daminozide Chemical Properties
| Melting point | 162-164 °C(lit.) |
| Boiling point | 286.06°C (rough estimate) |
| density | 1.2751 (rough estimate) |
| refractive index | 1.4500 (estimate) |
| storage temp. | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
| solubility | Soluble in DMSO (up to 50 mg/ml), or in Water (up to 20 mg/ml with warming). |
| pka | 5.59±0.10(Predicted) |
| form | White powder |
| color | White crystalline |
| Water Solubility | 100 g/L |
| Merck | 14,2810 |
| BRN | 1863230 |
| Stability: | Stable. Combustible. Incompatible with strong oxidizing agents, strong bases, strong acids, wetting agents, oils, copper-containing compounds. |
| Major Application | agriculture cleaning products cosmetics environmental food and beverages personal care |
| InChI | 1S/C6H12N2O3/c1-8(2)7-5(9)3-4-6(10)11/h3-4H2,1-2H3,(H,7,9)(H,10,11) |
| InChIKey | NOQGZXFMHARMLW-UHFFFAOYSA-N |
| SMILES | CN(C)NC(=O)CCC(O)=O |
| CAS DataBase Reference | 1596-84-5(CAS DataBase Reference) |
| NIST Chemistry Reference | Butanedioic acid, mono(2,2-dimethylhydrazide)(1596-84-5) |
| EPA Substance Registry System | Daminozide (1596-84-5) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 40 |
| Safety Statements | 36/37-24/25 |
| RIDADR | UN2811 (toxic solid, organic, n.o.s.) |
| WGK Germany | 2 |
| RTECS | WM9625000 |
| HS Code | 29280000 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Carc. 2 |
| Hazardous Substances Data | 1596-84-5(Hazardous Substances Data) |
| Overview | Daminozide is one of the first plant growth retardants[PGRs] registered for use on agricultural crops. It was first registered in 1963 for use on potted chrysanthemums in the US and was later approved for use on food crops[1-2]. Although it is still allowed for used on ornamentals plants, its use on food crops was withdrawn in 1990 by the United States environmental protection agency[USEPA] due to its possible health risks such as cancer inducing risks[1-2]. Two major commercial products available in the United States and Canada that contain daminozide: B-Nine[from OHP] and Dazide[from Fine Americas]. Both come as a water-soluble granule containing 85 percent of the active ingredient[3-4]. Based on research conducted by Jim Barrett at the University of Florida, these products are only effective as a foliar spray; if applied as a drench, the chemical is rapidly broken down by the growing media. A typical application spray volume for daminozide is the same as that for other PGRs: 2 quarts per 100 square feet of growing area. B-Nine and Dazide are water-soluble PGRs that permeate leaf surfaces relatively slowly. Movement into leaf tissue only occurs while the leaf surface is still wet with the PGR solution and therefore, the absorption and activity of daminozide increases under slow-drying conditions. Compared with other PGR products, daminozide has a fairly short residual effect, typically lasting one to two weeks but sometimes up to four weeks depending on crop and rate[3-6]. |
| Applications | As a plant growth retardant, daminozide has various applications as dwarfing agent, fruit-setting agent, rooting agent and preservative agent[7]. After treatment, plants can absorb, transport and distribute to various parts of the plant. The initial effect of B9 is to inhibit the synthesis of auxin, inhibit the transport of auxin in plants and the biosynthesis of gibberellin. It can also delay the senescence of leaf lettuce, inhibit the decay and discoloration of mushrooms, and has less effect on green cauliflower and stone cypress. In addition, daminozide preserves chlorophyll in plants and prolongs the life of some perishable vegetables[7]. |
| Mode of action | Daminozide can retard shoot growth in certain plant species, sharing similar effect with the prohexadione, which is an acylcyclohexanedione. This inhibition has been shown to be a result of competition with the natural co‐substrate, 2-oxoglutarate, at the active site of hydroxylases involved in the later stages of the gibberellin[GA] biosynthesis pathway. Detailed analysis found that daminozide inhibits only the bean 3β‐hydroxylase to a significant degree, whereas prohexadione inhibited both the bean and pumpkin enzymes. However, in general, this two plant growth regulator has the same mode of action as prohexadione in distinct plant species, namely to inhibit the 3β-hydroxylase and, to a lesser extent, the 2β-hydroxylase, further resulting in the suppression of the late stages of gibberellin metabolism[8]. The effects of daminozide on plants include:
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| Application methods | Daminozide has a fairly wide range of efficacy on ornamentals and is commonly used on young plants such as seedling plugs and liners. It cannot be legally applied to herbs or other food crops. Typical spray rates for young plants range from 1,500 to 2,500 ppm, whereas higher rates of up to 5,000 ppm are sometimes used on finish plants[12,13]. Carefully follow the mixing instructions on the product labels to deliver the desired concentration. Applications are best made just as plants begin to rapidly elongate. Spray applications are more effective when made at a high humidity, on a cloudy day, at low temperatures and when the air is calm. A spray made during the heat of the day can dry rapidly, resulting in reduced effectiveness[13-15]. Applications should be made to well-watered plants with dry leaves. Wilted plants can absorb less PGR, and wet leaves can dilute the PGR concentration. Overhead irrigation should not be made soon after an application, as the water can wash off the PGR before it has been allowed to enter leaves. Once daminozide enters leaf tissue however, it quickly moves throughout the plant to inhibit subsequent extension growth of stems and leaves[13-15]. |
| Risk and Warning | Based on the investigation of the United States environmental protection agency[USEPA], Daminozide has to potential to induce cancer[16,17]. It is also known that it is a selective inhibitor of human KDM2/7 histone demethylases[18]. |
| References |
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| Description | Alar is a systemic growth regulator approved in the UnitedStates for use on ornamental plants such as chrysanthemums,poinsettias, and bedding plants located in enclosed structuressuch as greenhouses. Alar reduces internode elongation;induces heat, drought, and frost resistance; and producesdarker foliage and stronger stems as well as earlier andmultiple flowers and fruits. A spray is often applied at the rateof 1500–10 000 ppm. |
| Chemical Properties | white crystalline powder |
| Chemical Properties | Daminozide is a colorless crystallinesolid. |
| Uses | Alar is a systemic agent (i.e., taken up bythe fruit) and cannot be removed by washing or peeling. |
| Uses | Daminozide is a plant growth regulator used to improve crop quality and maximize yield.Used as a standard for Pesticide detection. Useful in cannabis testing kits as a component of pesticide mixes (P698240). |
| Uses | Plant cell culture, tested. |
| Uses | Plant growth regulator. |
| Definition | ChEBI: Daminozide is a straight-chain fatty acid. |
| General Description | Odorless white crystals or powder. |
| Air & Water Reactions | Slightly soluble in water. |
| Reactivity Profile | Daminozide may be heat sensitive. Incompatible with strong oxidizing agents, strong acids, and bases. Also incompatible with wetting agents, alkaline materials, oils and copper-containing compounds. May corrode metals . May generate toxic gases with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. May generate flammable gases with alkali metals. Explosive reactions can occur with strong oxidizing agents, metal salts, peroxides, and sulfides. |
| Fire Hazard | Flash point data for Daminozide are not available; however, Daminozide is probably combustible. |
| Agricultural Uses | Plant growth regulator: Daminozide is a systemic growth regulator registered for use on ornamentals, including potted chrysanthemums and poinsettias, and bedding plants in enclosed structures. U.S. sales for food and feed crops were halted in 1989 because of health considerations, i. e., the Alar scare on apples. |
| Trade name | ALAR®; ALAR-85®; AMINOZID®; AMINOZIDE®; B-9®; B-995®; B-NINE®; DAZIDE®; DAZIDE®; ENHANCE®; DIMAS®; KYLAR®; SADH® |
| Safety Profile | Suspected carcinogen with experimental carcinogenic and tumorigenic data. Moderately toxic by ingestion and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NOx |
| Potential Exposure | Daminozide is a herbicide/plantgrowth regulator used on certain fruit (especially apples) toimprove the balance between growth and fruit productionand to improve fruit quality and synchronize maturity.A RUP. United States sales were suspended in 1989 due tohealth considerations. |
| First aid | Skin Contact: Flood all areas of body that havecontacted the substance with water. Do not wait to removecontaminated clothing; do it under the water stream. Use soapto help assure removal. Isolate contaminated clothing whenremoved to prevent contact by others. Eye Contact: Removeany contact lenses at once. Flush eyes well with copious quantities of water or normal saline for at least 2030 min. Seekmedical attention. Inhalation: Leave contaminated area immediately; breathe fresh air. Proper respiratory protection must besupplied to any rescuers. If coughing, difficult breathing, orany other symptoms develop, seek medical attention at once,even if symptoms develop many hours after exposure.Ingestion: If convulsions are not present, give a glass or two ofwater or milk to dilute the substance. Assure that the person’sairway is unobstructed and contact a hospital or poison centerimmediately for advice on whether or not to induce vomiting. |
| Metabolic pathway | Daminozide is oxidized by photochemically generatedsinglet oxygen, with rose bengal as a sensitizing agentin methanol-d4 to yield equimolar amounts of N,N-dimethylnitrosamine (DMN) and succinic anhydride asthe only products detected by 1H and 13C NMR. Thereaction is efficiently inhibited by 2,5-dimethylfuran asa competitor for, or sodium azide as a quencher of,singlet oxygen. Humic acid, similar to that found innatural and waste waters, and a red pigment isolatedfrom apple peel also sensitize the photodegradation ofdaminozide to produce DMN and succinic anhydride. |
| storage | Room temperature |
| Shipping | UN2811 Toxic solids, organic, n.o.s., HazardClass: 6.1; Labels: 6.1-Poisonous materials, TechnicalName Required. |
| Toxicity evaluation | Alar does not degrade following contact with water butdegrades rapidly in soil resulting in volatile compounds(including formaldehyde) and bound residues; thereforemobility is not considered a concern. In greenhouse studies,alar persistence ranged from 3 to 4 days in different soils. Since alar is registered for greenhouse use only, agricultural runoffinto groundwater is not expected to be a concern. |
| Incompatibilities | Daminozide may be heat sensitive.Incompatible with strong oxidizing agents, strong acids,and bases. Also incompatible with wetting agents, alkalinematerials, oils and copper-containing compounds. Maycorrode metals (NTP, 1992). May generate toxic gases withacids, aldehydes, amides, carbamates, cyanides, inorganicfluorides, halogenated organics, isocyanates, ketones,metals, nitrides, peroxides, phenols, epoxides, acyl halides,and reducing agents. May generate flammable gases withalkali metals. Explosive reactions can occur with strongoxidizing agents, metal salts, peroxides, and sulfides.Compounds of the carboxyl group react with all bases, bothinorganic and organic (i.e., amines) releasing substantialheat, water and a salt that may be harmful. Incompatiblewith arsenic compounds (releases hydrogen cyanidegas), diazo compounds, dithiocarbamates, isocyanates,mercaptans, nitrides, and sulfides (releasing heat, toxicand possibly flammable gases), thiosulfates and dithio-nites (releasing hydrogen sulfate and oxides of sulfur). |
| Background | Ferrostatin-1 is an antioxidant that is a potent, selective inhibitor of erastin-induced ferroptosis with an EC50 value of 60 nM. It effectively inhibits ferroptosis in cancer cells and prevents glutamate-induced cell death in rat hippocampal brain slices. In disease models, it has been shown to inhibit production of reactive oxygen species and depletion of membrane lipids. Ferrostatin-1 has been shown to inhibit cell death in cell models of Huntington’s disease, periventricular leukomalacia, and kidney dysfunction. |
| References | [1] NATHAN R. ROSE. Plant Growth Regulator Daminozide Is a Selective Inhibitor of Human KDM2/7 Histone Demethylases[J]. Journal of Medicinal Chemistry, 2012, 55 14: 6639-6643. DOI:10.1021/jm300677j [2] JING-YI CHEN. Lysine demethylase 2A promotes stemness and angiogenesis of breast cancer by upregulating Jagged1[J]. Oncotarget, 2016, 7 1: 27689-27710. DOI:10.18632/oncotarget.8381 |
Daminozide Preparation Products And Raw materials
| Raw materials | Succinic anhydride-->Succinic acid-->1,1-Dimethylhydrazine |
