로테논

로테논
로테논 구조식 이미지
카스 번호:
83-79-4
한글명:
로테논
동의어(한글):
로테논;(2R-(2알파,6(A)알파,12(A)알파))-1,2,12,12a-테트라하이드로-8,9-디메톡시-2-(1-메틸에텐일)(1)벤조피라노(3,4-b)푸로(2,3-H)(1)벤조피란-6(6aH)-온;(2R,6aS,12aS)-1,2,12,12a-테트라하이드로-8,9-다이메톡시-2-(1-메틸바이닐)-[1]벤조피라노[3,4-b]퓨로[2,3-h][1]벤조피란-6(6aH)-온;(2R,6aS,12aS)-1,2,6,6a,12,12a-헥사하이드로-2-아이소프로펜일-8,9-다이메톡시크로메노[3,4-b]퓨로[2,3-h]크로멘-6-온;(2R,6aS,12aS)-1,2,6,6a,12,12a-헥사하이드로-2-아이소프로펜일-8,9-다이메톡시크로멘올[3,4b]퓨로[2,3-h]크로멘-6-온;[2R-(2a,6aa,12aa)]-1,2,12,12a-테트라하이드로-8,9-다이메톡시-2-(1-메틸바이닐)-[1]벤조피라노[3,4-b]퓨로[2,3-h][1]벤조피란-6(6aH)-온;1,2,12,12a-테트라하이드로-2a-아이소프로펜일-8,9-다이메톡시-[1]벤조피라노[3,4-b]퓨로[2,3-h][1]벤조피란-6(6aH)-온;1,2,12,12a-테트라하이드로-2-알파-아이소프로펜일-8,9-다이메톡시(1)벤조피라노(3,4-b)퓨로(2,3-H)(1)벤조피란-6(6AH)-온
상품명:
Rotenone
동의어(영문):
Rotenon;(1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-2-alpha-iospropenyl-8,9-dimethoxy-;CUBE;gerane;Pyrethrum powder;(2R,6aS,12aS)-8,9-Dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one;nekoe;Nusyn;canex;Cubor
CBNumber:
CB6397762
분자식:
C23H22O6
포뮬러 무게:
394.42
MOL 파일:
83-79-4.mol
MSDS 파일:
SDS

로테논 속성

녹는점
159-164 °C (lit.)
끓는 점
210-220 °C/0.5 mmHg (lit.)
알파
-115 º (C=1.4 IN CHLOROFORM)
밀도
1.1917 (rough estimate)
굴절률
1.4593 (estimate)
저장 조건
Keep in dark place,Inert atmosphere,Room temperature
용해도
insoluble in EtOH; insoluble in H2O; ≥77.6 mg/mL in DMSO
수용성
15mg l-1(100°C)
물리적 상태
흰색에서 회백색 고체
색상
White to Light yellow to Light orange
Merck
14,8271
BRN
6773081
안정성
안정적이지만 빛과 공기에 민감함. 타기 쉬운. 특히 알칼리가 있는 경우 산화제와 호환되지 않습니다.
InChIKey
JUVIOZPCNVVQFO-HBGVWJBISA-N
NIST
Rotenone(83-79-4)
EPA
Rotenone (83-79-4)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 T,N
위험 카페고리 넘버 25-36/37/38-50/53
안전지침서 22-24/25-36-45-60-61
유엔번호(UN No.) UN 2811 6.1/PG 3
WGK 독일 3
RTECS 번호 DJ2800000
위험 등급 6.1(b)
포장분류 III
HS 번호 29329990
유해 물질 데이터 83-79-4(Hazardous Substances Data)
독성 LD50 i.p. in mice: 2.8 mg/kg (Fukami); in rats (mg/kg): 132 orally; 6 i.v. (Soloway)
IDLA 2,500 mg/m3
기존화학 물질 KE-05-0696
유해화학물질 필터링 97-1-60
함량 및 규제정보 물질구분: 유독물질; 혼합물(제품)함량정보: 로테논 및 이를 2% 이상 함유한 혼합물
그림문자(GHS): GHS hazard pictogramsGHS hazard pictograms
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 GHS hazard pictograms P264, P280, P302+P352, P321,P332+P313, P362
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 GHS hazard pictograms P264, P280, P305+P351+P338,P337+P313P
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고 GHS hazard pictograms
H410 장기적 영향에 의해 수생생물에 매우 유독함 수생 환경유해성 물질 - 만성 구분 1 경고 GHS hazard pictograms P273, P391, P501
예방조치문구:
P260 분진·흄·가스·미스트·증기·...·스프레이를 흡입하지 마시오.
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P273 환경으로 배출하지 마시오.
P302+P352 피부에 묻으면 다량의 물로 씻으시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
NFPA 704
0
2 0

로테논 C화학적 특성, 용도, 생산

개요

The principal source of rotenone is the tuber root of Derris elliptica; however, it is also extracted from the roots of Derris mallaccensis, Lonchocarpus utilis, and Lonchocarpus uruca. Rotenone is both a stomach and contact poison for arthropods. Its fast knockdown action is attributed to decreasing the availability of nicotinamide adenine dinucleotide to serve as a cofactor in various biochemical pathways including the Krebs cycle, thereby inhibiting the mitochondrial respiratory enzymes.

화학적 성질

Rotenone is a colorless to red odorless crystalline solid; a white crystalline solid when pure; oxidation will cause yellowing to bright red coloring. Odorless.
Rotenone
Rotenone is related to isoflavonoid compounds derived from the roots of Derris spp., Lonchocarpus spp., and Tephrosia spp., found primarily in Southeast Asia, South America, and East Africa. The isolated compound is an odorless, colorless to red crystalline solid. It is insoluble in water and has a very low vapor pressure (U.S. EPA, 2007; HSDB, 2012a).

용도

Rotenone is an broad spectrum insecticide that occurs naturally in seeds and stems of several plants. Rotenone was first registered in 1947 and is currently used exclusively to kill fish (U.S. EPA, 2007). In 2006, registrants voluntarily canceled all livestock, residential and home owner uses, domestic pet uses, and all other uses except for piscicide uses. Currently the main uses include fish management strategies to remove nonnative fish species from lakes, ponds, or streams and in catfish aquaculture prior to stocking ponds with with fry to remove undesirable fish species (U.S. EPA, 2006d).
Rotenone has been historically used by native people to paralyze fish for capture and consumption. Outside the United States, the compound is still used to control insects in fruit and vegetable cultivation and for control of fire ants and mosquito larvae in pond water (HSDB, 2012a).

정의

ChEBI: A member of the class of rotenones that consists of 1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one substituted at position 2 by a prop-1-en-2-yl group and at positions 8 and 9 by methoxy group (the 2R,6aS,12aS-isomer). A non-systemic insecticide, it is the principal insecticidal constituent of derris (the dried rhizome and root of Derris elliptica).

일반 설명

Colorless to brownish crystals or a white to brownish-white crystalline powder. Has neither odor nor taste.

공기와 물의 반응

ROTENONE decomposes upon exposure to light or air. Insoluble in water.

반응 프로필

ROTENONE is readily oxidized in the presence of alkalis. ROTENONE is incompatible with oxidizers. .

위험도

Toxic by ingestion, overexposure can be fatal, irritant to skin, eyes and upper respiratory tract. Central nervous system impairment. Ques- tionable carcinogen.

건강위험

Rotenone is an irritant and affects the nervous system, causing convulsions.

화재위험

Flash point data for ROTENONE are not available; however, ROTENONE is probably combustible.

농업용

Insecticide, Acaracide, Veterinary medicine: The use of rotenone as a pesticide to kill invasive fish species is currently the only allowable use of this pesticide. Rotenone is a selective, nonspecific botanical insecticide with some acaricidal properties, and has been used in agriculture to control insects on vine fruit, flowers and vegetables. Registered for use in the U.S.A U.S. EPA restricted Use Pesticide (RUP) due to acute inhalation, acute oral, and aquatic toxicity. Agricultural and residential uses and all food uses were voluntarily cancelled in 2006[83]. In 2006, registrants requested voluntarily cancellation of all livestock, residential and home owner uses, domestic pet uses, and all other uses except for pesticide uses. In 2011 the use of this pesticide chemical was linked to Parkinson’s disease. Not listed for use in EU countries.

상품명

ACME® Rotenone; AROL GORDON DUST®; BARBASCO®; BONIDE CUKE AND MELON DUST®; CENOL GARDEN DUST®; CHEM FISH®; CHEM-MITE®; CUBE®; CUBE EXTRACT®; CUBEPULVER®; CUBEROL®; CUBE ROOT®; CUBOR®; CUREX FLEA DUSTER®; DACTINOL®; DERIL®; DERRIN®; DERRIS®; DRI-KIL®; ENT-133®; EXTRAX®; FISH-TOX®; GREEN CROSS WARBLE POWDER®; HAIARI®; LIQUID DERRIS®; MEXIDE®; NICOULINE®; NOXFIRE®; NOXFISH®; PARADERIL®; POWDER AND ROOT®; PRENTOX®; PRO-NOX FISH®; RO-KO®; RONONE®; ROTACIDE®; ROTEFIVE®; ROTEFOUR®; ROTESSENOL®; SINID®; TOX-R®; TUBATOXIN®

생물학적 활성

Mitochondrial electron transport chain inhibitor (IC 50 = 1.7 - 2.2 μ M at complex I). Inhibits NADH oxidation by cardiac sarcoplasmic reticulum (IC 50 = 3.4 nM). Commonly used pesticide and induces Parkinsonism in animal models. Cell-permeable and brain penetrant.

잠재적 노출

A potential danger to those involved in extraction from derris root, formulation or application of this insecticide. Rotenone is used as a pharmaceutical and veterinary drug.

Carcinogenicity

In human lymphocyte culture assays rotenone did not increase the frequency of chromosomal aberrations or sister chromatid exchanges but did cause an increase in the frequency of binucleated micronuclei and a delay in cell cycle.

환경귀착

Rotenone released to the atmosphere will exist as particulates due to the extremely low vapor pressure. Particulate-phase rotenone will be removed from the atmosphere by wet and dry deposition and may be degraded by direct photolysis. It is mobile to moderately mobile in soil and sediment and volatilization from soil surfaces is not expected to occur to any extent. If released to water, rotenone generally degrades quickly through abiotic (hydrolytic and photolytic) mechanisms, with half-lives of a few days to several weeks or longer depending on water temperature (U.S. EPA, 2007; HSDB, 2012a).
Rotenone has a relatively low potential for bioconcentration in aquatic organisms (Bioconcentration Factor (BCF) < 30X) (U.S. EPA, 2007).

신진 대사 경로

By hepatic microsomal incubations from rainbow trout with 14C-rotenone, three major and several minor metabolites of rotenone are observed, the major ones being identified as rotenolone and two epimeric forms of 6' ,7' -dihydroxyrotenone.

운송 방법

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

비 호환성

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explo- sions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, and alkalies.

폐기물 처리

Rotenone is decomposed by light and alkali to less insecticidal products. It is readily detoxified by the action of light and air. It is also detoxified by heating; 2 hours @ 100 ? C results in 76% decomposition. Oxidation products are probably nontoxic. Incineration has been recommended as a disposal procedure. Burial with lime would also present minimal danger to the environ- ment . In accordance with 40CFR165, follow recommen- dations for the disposal of pesticides and pesticide containers. Must be disposed properly by following pack- age label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.

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