(2E,4E)-3,7,11-トリメチル-2,4-ドデカジエン酸エチル

Hydroprene

HCID 5372477

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

Hydroprene41096-46-2Gencorethyl (2E,4E)-3,7,11-trimethyldodeca-2,4-dienoate(2E,4E)-HydropreneAltozar IGRZR 512Ethyl (2E,4E)-3,7,11-trimethyl-2,4-dodecadienoateGENTROLEGYT 2669OMS 1696ENT 70459
名称をさらに表示
(2E,4E)-3,7,11-トリメチル-2,4-ドデカジエン酸エチルヒドロプレンアルトザル(2E,4E)-3,7,11-トリメチルドデカ-2,4-ジエン酸エチルアルトザルIGRエチル (2E,4E)-3,7,11-トリメチルドデカ-2,4-ジエノアートzr512oms1696altozarent70459Hydroprene=Altozar=Encotone=Gencorethyl3,7,11-trimethyldodeca-2,4-dienoate
Ethyl 3,7,11-trimethyl-trans-2,trans-4-dodecadienoateEthyl (E,E)-(+-)-3,7,11-trimethyl-2,4-dodecadienoate3SS174B1Y9ZR-512DTXSID9042049CHEBI:39234OMS-1696SHA-486300

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

実験および物理化学的性質

Pesticides · 2 件

Pesticides -> Other Insecticides

Pesticide (Hydroprene) -> USDA PDB

Color/FormAmber liquid
SolubilityIn water, 0.54 mg/l. Soluble in common organic solvents.
Vapor Pressure · 2 件

0.000188 [mmHg]

25 mPa at 25 °C

Physical DescriptionAmber liquid; [HSDB]

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

Other Safety InformationIMAP assessments - 2,4-Dodecadienoic acid, 3,7,11-trimethyl-, ethyl ester, (E,E)-: Environment tier I assessment
Hazards SummaryNOAEL = 250 mg/kg in 28 day feeding study of rats; Not mutagenic in mice at 1300 mg/kg; Not teratongenic in rabbits at 90 mg/kg; [HSDB]
FIFRA RequirementsA tolerance is established permitting the use of the insect growth regulator hydroprene ... and (S)-hydroprene, in food handling establishments in accordance with certain perscribed conditions. ...
Skin, Eye, and Respiratory IrritationsMinimal eye, no skin irritation.

安全と保護具

Preventive Measures · 1 件

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 ExcerptsIn 28 day feeding trials in rats no-effect level was 250 mg/kg. No mutagenic activity was observed in mice at 1300 mg/kg nor teratogenic effect in rabbits at 90 mg/kg daily (highest doses tested).
Evidence for CarcinogenicityCancer Classification: Group D Not Classifiable as to Human Carcinogenicity
Toxicity DataLC50 (rat) > 5,400 mg/m3
Acceptable Daily IntakesOPP RfD= 0.02 mg/kg.
Non-Human Toxicity Values · 3 件

LD50 Rat oral >5100 mg/kg

LD50 Dog oral >10,000 mg/kg

LD50 Rabbit percutaneous >5100 mg/kg

法規制情報

FIFRA RequirementsA tolerance is established permitting the use of the insect growth regulator hydroprene ... and (S)-hydroprene, in food handling establishments in accordance with certain perscribed conditions. ...

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

Mechanism of ActionInsect growth regulator (juvenile hormone mimic), preventing metamorphosis to viable adult when applied to larval stage.
Metabolism/Metabolites · 2 件

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 · 4 件

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.

Formulations/PreparationsEmulsifiable concentrate; aerosol, cold fogging concentrate.

応用分野

使用Hydroprene is used in the method for controlling pests of sugarcane, citrus, rapeseed, and potato plants.

サプライヤー1 社

常州安轩化工有限公司13912302692 · [email protected]

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

1 件

化合物ノート

読み込み中…