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(1R)-2β-(2-メチル-1-プロペニル)-3,3-ジメチルシクロプロパン-1α-カルボン酸3-(フェノキシ)ベンジル

Phenothrin, trans-(-)-

HCID 91581
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
26046-85-5
標準SMILES
CC(C)=C[C@@H]1[C@@H](C(=O)OCc2cccc(Oc3ccccc3)c2)C1(C)C
InChIKey
SBNFWQZLDJGRLK-RTWAWAEBSA-N
分子式
C23H26O3
平均分子量
350.4 g/mol
単同位体質量
350.18819469

概要

(1R)-trans-phenothrin is a phenothrin. It is functionally related to a (+)-trans-chrysanthemic acid.

名称と識別子

優先名称
Phenothrin, trans-(-)-
IUPAC
cis-(3-phenoxyphenyl)methyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
現地名
(1R)-2β-(2-メチル-1-プロペニル)-3,3-ジメチルシクロプロパン-1α-カルボン酸3-(フェノキシ)ベンジル
英語名
D-Phenothrin
分子式
C23H26O3
分子量
350.45

名称と別名

(-)-trans-Phenothrin6JX527V7HJ1R,3R-PHENOTHRINDTXSID1058347(1R-TRANS)-BIOPHENOTHRINPHENOTHRIN, TRANS-(-)-m-Phenoxybenzyl (1R-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylateCYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3-(2-METHYL-1-PROPENYL)-, (3-PHENOXYPHENYL)METHYL ESTER, (1R,3R)-RefChem:861495DTXCID50320783-Phenoxybenzyl (-)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylateCyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (3-phenoxyphenyl)methyl ester, (-)-trans-
名称をさらに表示
(1R,3R)-2,2-ジメチル-3-(2-メチル-1-プロペニル)シクロプロパンカルボン酸3-フェノキシベンジル(1R)-3,3-ジメチル-2β-(2-メチル-1-プロペニル)シクロプロパン-1α-カルボン酸3-フェノキシベンジル(1R)-2β-(2-メチル-1-プロペニル)-3,3-ジメチルシクロプロパン-1α-カルボン酸3-(フェノキシ)ベンジル(1R)-2,2-ジメチル-3α-(2-メチル-1-プロペニル)シクロプロパン-1β-カルボン酸3-フェノキシベンジル(1R)-2β-(2-メチル-1-プロペニル)-3,3-ジメチルシクロプロパン-1α-カルボン酸m-フェノキシベンジル(1R,3R)-2,2-ジメチル-3α-(2-メチル-1-プロペニル)シクロプロパンカルボン酸(3-フェノキシフェニル)メチルD-TRANS-フェノトリン標準品

物性

構造計算による物性

XLogP
6.2
極性表面積
35.5 Ų
水素結合供与体数
0
水素結合受容体数
3
回転可能結合数
7
重原子数
26
形式電荷
0
複雑度
512

実験および物理化学的性質

Endocrine DisruptorsPotential endocrine disrupting compound

物理化学的性質

沸点
437 · 437.0±45.0 °C(Predicted)
比重(密度)
1.12 · 1.120±0.06 g/cm3(Predicted)
蒸気圧
1.9 · 1.9×10-5Pa (21.4 °C)
貯蔵温度
2 · Sealed in dry,2-8°C
溶解性
Chloroform (Slightly), Methanol (Slightly)
外見
Oil
水溶解度
-1 · -1 (25 °C)
色
Colourless to Dark Yellow
CAS データベース
26046 · 26046-85-5(CAS DataBase Reference)
EPAの化学物質情報
d-Phenothrin (26046-85-5)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 4.3% (1 of 23) of reports.

Warning

H400 (95.7%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

P273, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 23 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information1R-trans-phenothrin: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAquatic Acute 1 (95.7%)

毒性情報

Treatment · 1 件

Following oral exposure, the treatment is symptomatic and supportive and includes monitoring for the development of hypersensitivity reactions with respiratory distress. Provide adequate airway management when needed. Gastric decontamination is usually not required unless the pyrethrin product is combined with a hydrocarbon. Following inhalation exposure, move patient to fresh air. monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility. If the contamination occurs through dermal exposure, Remove contaminated clothing and wash exposed area thoroughly with soap and water. A physician may need to examine the area if irritation or pain persists. Vitamin E topical application is highly effective in relieving parenthesis. (L363)

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

d-Phenothrin is a fast acting insecticide, effective by contact and stomach action. It is rapidly metabolized and excreted by humans and has low human toxicity. For both cis- and trans- isomers, the product was metabolized by hydrolysis, oxidation and conjugation and a large part of d-Phenothrin is excreted unchanged in the urine and the faeces. Following oral administration of the (1R)- trans - isomer, the urine is the major excretory route. The isomer is extensively metabolized to oxidative and conjugated derivatives of the hydrolysed ester. Oxidative and conjugated derivatives of the (1R)- cis -isomer are also observed but hydrolysis of the ester linkage is a minor metabolic pathway. With this isomer the faeces is the major excretory route. The metabolic profiles aree similar following dermal application, although the rates of excretion for each isomer showed some differences between the two routes of administration. The major metabolite is 3-phenoxybenzyl alcohol (PBalc). Smaller amounts of PBacid and trace amounts of 4'-OH-PBacid are also found. It is stable to storage in the dark; d-Phenothrin is relatively unstable to sunlight or ultra violet irradiation, or in alkaline media. (L866, A561)

用途と製造

UsesPyrethroids are used as insecticides. (L857)

応用分野

使用Phenothrin is used for the control of insects for public health. It is also used to protect stored grain.

関連反応

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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
D‐TRANS‐フェノトリン標準品
ビオフェノトリン
2,2-ジメチル-3α-(2-メチル-1-プロペニル)シクロプロパン-1β-カルボン酸3-フェノキシベンジル
(3-フェノキシフェニル)メチル (1R,3R)-2,2-ジメチル-3-(2-メチルプロパ-1-エン-1-イル)シクロプロパン-1-カルボキシラート
D-PHENOTHRIN
D-permethrin
D-trans-Phenot
rich-d-t-Phenothrin
Pesticide D-Phenothrin
(1r-trans)-henyl)methyleste
D-Phenothrin, 10 mM in DMSO
26046-85-5(1R)-trans-Phenothrind-trans-Phenothrin1R-trans-Phenothrinphenothrin [(1R)-trans- isomer](3-phenoxyphenyl)methyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylateCyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (3-phenoxyphenyl)methyl ester, (1R-trans)-C23H26O3

データベース識別子

CAS
26046-85-5、51186-86-8
PubChem CID
91581
DTXSID
DTXSID1058347
ChEBI
CHEBI:39405
UNII
6JX527V7HJ
EC Number
247-431-2
Nikkaji
J246.546I
Health Effects · 1 件

Pyrethroid effects typically include rapid onset of aggressive behavior and increased sensitivity to external stimuli, followed by fine tremor, prostration with coarse whole body tremor, elevated body temperature, coma, and death. Paresthesia, severe corneal damage, hypotension and tachycardia, associated with anaphylaxis, can also occur following pyrethriod poisoning. (L857)

Exposure RoutesInhalation (L857); oral (L857); dermal (L857) ; eye contact (L857).
Toxicity Summary · 1 件

Both type I and type II pyrethroids exert their effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. They appear to bind to the membrane lipid phase in the immediate vicinity of the sodium channel, thus modifying the channel kinetics. This blocks the closing of the sodium gates in the nerves, and thus prolongs the return of the membrane potential to its resting state. The repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential produces effects quite similar to those produced by DDT, leading to hyperactivity of the nervous system which can result in paralysis and/or death. Other mechanisms of action of pyrethroids include antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, and actions on calcium ions. They also inhibit calium channels and Ca2+, Mg2+-ATPase. (T10, T18, L857)

Signs and Symptoms · 1 件

Following oral exposure, severe fine tremor, marked reflex hyperexcitability, sympathetic activation can occur. Nausea, vomiting and abdominal pain commonly occur and develop following ingestion. Sudden bronchospasm, swelling of oral and laryngeal mucous membranes, and anaphylactoid reactions have been reported after inhalation. Hypersensitivity reactions characterized by pneumonitis, cough, dyspnea, wheezing, chest pain, and bronchospasm may occur too . Dermatitis is the main effect of a dermal exposure to phenothrin. (T36)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataLD50: > 5000 mg/kg (Oral, Rat) (A561) LD50: 10 000 mg/kg (Dermal, Rat) (A561)

安全データ

毒性
LD50 oral in mouse: > 10gm/kg
消防法
危-4-3-III