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Valone

HCID 6733
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
83-28-3
Standard SMILES
CC(C)CC(=O)C1C(=O)c2ccccc2C1=O
InChIKey
PVWMAOPFDINGAY-UHFFFAOYSA-N
Molecular formula
C14H14O3
Average molar mass
230.26 g/mol
Monoisotopic mass
230.0942943

Overview

structure in first source

Names & identifiers

Preferred name
Valone
IUPAC
2-(3-methylbutanoyl)indene-1,3-dione
English name
2-Isovaleryl-1,3-indanedione
Molecular formula
C14H14O3
Molecular weight
230.26

Names & synonyms

VALONE83-28-32-Isovaleryl-1,3-indanedioneIsovalIsovaleryl indandioneMotomco tracking powder2-Isopentanoyl-1,3-indanedioneCaswell No. 5152-Isovalerylindane-1,3-dioneNSC 404427DTXSID8042509EPA Pesticide Chemical Code 067702
Show more names
PMP(R)NSC-5754AI300366VALONE(R)AI3 00366
NSC-404427BRN 21163742V8VCY004EAI3-00366DTXCID60225094-07-00-02791 (Beilstein Handbook Reference)RefChem:193602201-464-9

Database identifiers

CAS
83-28-3
PubChem CID
6733
DTXSID
DTXSID8042509
ChEMBL
CHEMBL3186888
UNII
2V8VCY004E
EC Number
201-464-9
Nikkaji
J127.616F

Properties

Computed structural properties

XLogP
2.6
Topological polar surface area
51.2 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
3
Heavy atoms
17
Formal charge
0
Complexity
332

Experimental & physicochemical properties

DrugsPharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
Pesticides · 3 items

Rodenticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Rodenticides, Anticoagulant

Color/Form · 2 items

Yellow, crystalline solid.

Yellow solid from methanol

SolubilityInsoluble in water; soluble in common organic solvents.
Melting Point68-69 °C
Vapor Pressure0.00000688 [mmHg]
Physical DescriptionYellow solid; [Merck Index] Yellow crystalline solid; [MSDSonline]
Collision Cross Section154.2 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID8042509]

Physicochemical properties

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Regulatory Information2004/129/EC
Hazards SummaryA vitamin K antagonist--causes disruption of clotting factors and bleeding; [HSDB] An indandione anticoagulant rodenticide; [INCHEM] See Warfarin.
Special ReportsWHO; Environ Health Criteria 175: Anticoagulant Rodenticides (1995)
FIFRA Requirements · 1 item

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. 2-Isovaleryl-1,3-indandione is found on List B. Case No: 2825; Pesticide type: rodenticide; Case Status: No products containing the pesticide are actively registered. Therefore, we are characterizing the case as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): 2-Isovaleryl-1,3-indandione; AI Status: The active ingredient is no longer contained in any registered products ... "cancelled."

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

Both 4-hydroxycoumarin derivatives and indandiones (also known as oral anticoagulants) are antagonists of vitamin K. Their use as rodenticides is based on the inhibition of the vitamin K-dependent step in the synthesis of a number of blood coagulation factors. The vitamin K-dependent proteins involved in the coagulation cascade are the procoagulant factors II (prothrombin), VII (proconvertin), IX (Christmas factor) and X (Stuart-Prower factor), and the coagulation-inhibiting proteins C and S. All these proteins are synthesized in the liver. Before they are released into the circulation the various precursor proteins undergo substantial (intracellular) post-translational modification. Vitamin K functions as a co-enzyme in one of these modifications, namely the carboxylation at well-defined positions of 10-12 glutamate residues into gamma-carboxyglutamate (Gla). The presence of these Gla residues is essential for the procoagulant activity of the various coagulations factors. Vitamin K hydroquinone (KH2) is the active co-enzyme, and its oxidation to vitamin K 2,3-epoxide (KO) provides the energy required for the carboxylation reaction. The epoxide is than recycled in two reduction steps mediated by the enzyme KO reductase. The latter enzyme is the target enzyme for coumarin anticoagulants. Their blocking of the KO reductase leads to a rapid exhaustion of the supply of KH2, and thus to an effective prevention of the formation of Gla residues. This leads to an accumulation of non-carboxylated coagulation factor precursors in the liver. In some cases these precursors are processed further without being carboxylated, and (depending on the species) may appear in the circulation. At that stage the under-carboxylated proteins are designated as descarboxy coagulation factors. Normal coagulation factors circulate in the form of zymogens, which can only participate in the coagulation cascade after being activated by limited proteolytic degradation. Descarboxy coagulation factors have no procoagulant activity (i.e. they cannot be activated) and neither they can be converted into the active zymogens by vitamin K action. Whereas in anticoagulated humans high levels of circulating descarboxy coagulation factors are detectable, these levels are negligible in warfarin-treated rats and mice. /Anticoagulant rodenticides/

Uses & manufacturing

Uses · 6 items

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Melting point
68 · 68-69 °C
Boiling point
312.25 °C · 312.25°C (rough estimate)
Density
1.1914 · 1.1914 (rough estimate)
refractive index
1.5557 · 1.5557 (estimate)
pka
3.12 · 3.12±0.10(Predicted)
FDA UNII
2 V8VCY004E · 2V8VCY004E
EPA Substance Registry System
Valone (83-28-3)
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
335 · H335-H315-H319
Precautionary statements
264 · P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
RIDADR
3027 · 3027
HazardClass
6.1 · 6.1(b)
PackingGroup
III
Hazardous Substances Data
83 · 83-28-3(Hazardous Substances Data)

Safety & protection

Disposal Methods · 1 item

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Toxicology

Interactions · 2 items

The following drugs ... may increase ... response to coumarin or indandione derivatives: alcohol (acute intoxication), allopurinol, aminosalicylic acid, amiodarone, anabolic steroids, chloral hydrate, chloramphenicol, cimetidine, clofibrate, co-trimoxazole, danazol, dextrothyroxine sodium, diazoxide, diflunisal, disulfiram, erythromycin, ethacrynic acid, fenoprofen calcium, glucagon, ibuprofen, indomethacin, influenza virus vaccine, isoniazid, meclofenamate, mefenamic acid, methylthiouracil, metronidazole, miconazole, nalidixic acid, neomycin (oral), pentoxifylline, phenylbutazone, propoxyphene, propylthiouracil, quinidine, quinine, salicylates, streptokinase, sulfinpyrazone, sulfonamides, sulindac, tetracyclines, thiazides, thyroid drugs, tricyclic antidepressants, urokinase, vitamin E. /Coumarin & indandione derivatives/

The following drugs ... may ... decrease ... response to coumarin or indandione derivatives: alcohol (chronic alcoholism), barbiturates, carbamazepine, corticosteroids, corticotropin, ethchlorvynol, glutethimide, griseofulvin, mercaptopurine, methaqualone, oral contraceptives containing estrogen, rifampin, spironolactone, vitamin K. /Coumarin & indandione derivatives/

Ecotoxicity Excerpts · 1 item

/ACCIDENTAL POISONINGS/ /In domestic animals,/ signs of poisoning occur after a latent period of 12 hr to several days and may include: bruising easily with occasional nose or gum bleeds; blood in stools or urine; excessive bleeding from minor cuts or abrasions; labored breathing; pale mouth and cold gums; anorexia and general weakness. A reliable indication of an anticoagulant effect is the determination of prothrombin time. /Anticoagulant rodenticides/

Human Toxicity Excerpts · 1 item

/HUMAN EXPOSURE STUDIES/ Typical features of poisoning result from increased bleeding tendency and include: minor poisoning: coagulation disturbance detected only by laboratory analyses; moderate poisoning: coagulation disturbance resulting in hematomata, hematuria, blood in feces or excessive bleeding from minor cuts or abrasions, gum bleeding; severe poisoning: retroperitoneal hemorrhage, severe GI bleeding, cerebrovascular accidents, massive hemorrhage (internal bleeding) resulting in shock. If anaemia or liver disease is present then the above features may be more severe and persistent and the poisoning may be more difficult to control. The onset of the signs of poisoning may not be evident until a few days after ingestion. /Anticoagulant rodenticides/

Populations at Special RiskSRP: Persons with bleeding disorders or who are taking anticoagulants should be protected from exposure.
Antidote and Emergency Treatment · 1 item

Human exposure to second-generation and indandione anticoagulants produces symptoms consistent with anticoagulation effects (e.g., hematomas, hematemesis, hematuria, easy bruisability). Treatment of cases of exposure, particularly of substantial and repeated exposure, may require vitamin K1 therapy and monitoring of prothrombin times for periods of many months.

Regulatory information

FIFRA Requirements · 1 item

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. 2-Isovaleryl-1,3-indandione is found on List B. Case No: 2825; Pesticide type: rodenticide; Case Status: No products containing the pesticide are actively registered. Therefore, we are characterizing the case as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): 2-Isovaleryl-1,3-indandione; AI Status: The active ingredient is no longer contained in any registered products ... "cancelled."

Safety data

ridadr
3027
Signal word
Warning
Symbol(GHS)
GHS07
hazard_class
6.1(b)
packing_group
III
Hazard statements
H335-H315-H319
Precautionary statements
P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
Hazardous Substances Data
83-28-3(Hazardous Substances Data)

Used as rodenticide and insecticide; [Merck Index]

Cancelled--no longer registered as a pesticide for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

The active ingredient is no longer contained in any registered products ... "cancelled."

For 2-isovaleryl-1,3-indandione (USEPA/OPP Pesticide Code: 067702) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Rodenticide

Formulations/PreparationsTrade Names: Valone, PMP Tracking Powder.

Applications

UsesValone is an intermediate in the preparation of diorganotin(IV) complexes.

Suppliers18 total

上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
南通市苏北化工原料有限公司0513-85290972 18762756250 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
上海泰坦科技股份有限公司13023226327 · [email protected]
深圳市丽晶生化科技有限公司0755-85201366 18938635012 · [email protected]
career henan chemical co+86-0371-86658258 · [email protected]
深圳利斯康医药科技有限公司+86-755-89396905 +86-15013857715 · [email protected]
湖北玖天生物医药科技有限公司027-88013699 17354350817 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
SUZHOU SENFEIDA CHEMICAL CO.,LTD+86-0512-83500002 +86-15195660023 · [email protected]
陕西缔都医药有限责任公司81148925 17391631969 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
上海杰股生物科技有限公司021-51698675 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]
南通众合化工新材料有限公司0513-85666561 15950816326 · [email protected]