基本情報
- CAS
36557-30-9- 標準SMILES
CCOC(=O)/C=C(C)/C=C/CC(C)CCCC(C)C- InChIKey
FYQGBXGJFWXIPP-UEVLXMDPSA-N- 分子式
- C17H30O2
- 平均分子量
- 266.4 g/mol
- 単同位体質量
- 266.2245802
概要
Hydroprene is the ethyl ester of (2E,4E)-3,7,11-trimethyldodeca-2,4-dienoic acid. It has a role as a juvenile hormone mimic. It is an ethyl ester and a farnesane sesquiterpenoid.
名称と識別子
- 優先名称
- Hydroprene
- IUPAC
- ethyl (2E,4E)-3,7,11-trimethyldodeca-2,4-dienoate
- 現地名
- (2E,4E)-3,7,11-トリメチル-2,4-ドデカジエン酸エチル
- 英語名
- HYDROPRENE
- 分子式
- C17H30O2
- 分子量
- 266.42
名称と別名
名称をさらに表示
データベース識別子
- CAS
36557-30-9、41096-46-2、41205-09-8- PubChem CID
- 5372477
- DTXSID
DTXSID9042049- ChEMBL
CHEMBL37754- ChEBI
CHEBI:39234- UNII
- 3SS174B1Y9
- EC Number
- 609-897-9
- Nikkaji
- J16.016D、J91.197F
物性
構造計算による物性
- XLogP
- 6.2
- 極性表面積
- 26.3 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 2
- 回転可能結合数
- 10
- 重原子数
- 19
- 形式電荷
- 0
- 複雑度
- 300
実験および物理化学的性質
Pesticides
Pesticides -> Other Insecticides
Pesticide (Hydroprene) -> USDA PDB
Vapor Pressure
0.000188 [mmHg]
25 mPa at 25 °C
物理化学的性質
- 沸点
- 0.03 · bp0.03 95°
- 比重(密度)
- 0.8955 · 0.8955
- 屈折率
- 1.451 · 1.4510 (estimate)
- Henry's Law Constant
- 5.1 · 5.1×10-2 mol/(m3Pa) at 25℃, Ebert et al. (2023)
- EPAの化学物質情報
- Hydroprene (41096-46-2)
安全と法規制
危険有害性情報
安全と保護具
Preventive Measures
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
毒性情報
Non-Human Toxicity Values
LD50 Rat oral >5100 mg/kg
LD50 Dog oral >10,000 mg/kg
LD50 Rabbit percutaneous >5100 mg/kg
法規制情報
安全データ
- 毒性
- LD50 orally in rats: >34000 mg/kg (Edwards)
- hs_code
- 29161900
- 有毒物質データの
- 41096-46-2(Hazardous Substances Data)
化学と産業
薬理情報
Metabolism/Metabolites
Microsomal oxidases and esterases prepared from houseflies, flesh flies and blow flies produced the same metabolites. These have been identified as: the free acid; the epoxide; the epoxy-acid; and the diol-acid. The position of the epoxy was not firmly established as 4,5 and may result from reaction of the 2,3-double bond. Some conjugated metabolites were observed but not identified. Part of these were converted to hydroprene acid by the use of sulfatase and beta-glucosidase. Oxidative metabolism of hydroprene was increased fourfold by phenobarbital in the diet of adult houseflies. There was not effect on the activity of the esterase system. Houseflies, flesh flies and blow flies, in vivo and in vitro, metabolized hydroprene. Two types of microsomal enzymes seemed to be involved in vitro. In the absence of the reduced form of nicotinamide-adenine dinucleotide phosphate, cochromatography in TLC and GLC systems showed the presence of the free acid, indicating an esterase activity. Inclusion of the reduced form of nicotinamide-adenine dinucleotide phosphate gave three more peaks. The data indicated these to be the 4,5 (or 2,3) hydroprene epoxide, the epoxy-acid and the diol-acid.
In Manduca sexta larvae, a binding protein acts as a carrier for the /juvenile hormone including hydroprene/. This prevents hydrolyses by general esterases present in the tissues and protects the juvenile hormone. The juvenile hormone-esterases are specific and distinct from the general esterases present in the hemolymph of Manduca sexta larvae. The specific enzyme was found in the fat body and target tissues. The binding of juvenile hormones to proteins was investigated with juvenile hormone-1, methoprene and Bowers' 2b. These compounds exhibited binding constants of 10(5) to 10(6) M(-1) with indication that the binding was electrostatic in nature. With oxidized cytochrome p450, Type I complexes formed.
用途と製造
Uses
Used as insect growth regulator and insecticide; [Merck Index] Used as an insecticide against immature cockroaches and weevils; [REPROTOX] Prevent metamorphosis from larval stage to adult; [HSDB]
Farming (Pesticides) [Category: Industry]
Insect growth regulator.
Control of Coleoptera, Homoptera, and Lepidoptera. Also control of cockroaches in residential buildings and non-food areas of industrial and commercial premises.
応用分野
使用Hydroprene is used in the method for controlling pests of sugarcane, citrus, rapeseed, and potato plants.
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補足説明
定義ChEBI: The ethyl ester of (2E,4E)-3,7,11-trimethyldodeca-2,4-dienoic acid
関連反応
化合物ノート
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