로테논

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

https://huagongshe.com/ko/chemical/6758

식별자 및 물리적 특성

CAS No.	83-79-4
분자식	C23H22O6
평균 분자량	394.4 g/mol
단동위원소 질량	394.14163842 g/mol
SMILES	C=C(C)[C@H]1Cc2c(ccc3c2O[C@@H]2COc4cc(OC)c(OC)cc4[C@@H]2C3=O)O1
InChIKey	JUVIOZPCNVVQFO-HBGVWJBISA-N
PubChem CID	6758
ChEMBL	CHEMBL429023
ChEBI	CHEBI:28201
EC No.	201-501-9
DTXSID	DTXSID6021248
현지명	로테논

화학 및 물리적 성질

XLogP	4.1
극성 표면적	63.2
수소 결합 공여자 수	0
수소 결합 수용자 수	6
회전 가능 결합 수	3
무거운 원자 수	29
형식 전하	0
복잡도	664
의약품	Pharmaceuticals -> Listed in ZINC15
지질	Polyketides [PK] -> Flavonoids [PK12] -> Rotenoid flavonoids [PK1206]
농약	Pesticide -> EPA IRISInsecticidesActive substance -> EU Pesticides database: Not approvedPesticides -> Other InsecticidesVeterinary substances, Acaricides, InsecticidesPesticide (Rotenone) -> USDA PDB
LogP(분배 계수)	log Kow = 4.10
냄새	Odorless
밀도	1.27 at 68 °F (NTP, 1992) - Denser than waterwill sink1.27 at 20 °C1.27 g/cm³1.27 @ 20°C1.1917 (rough estimate)
Color/Form	Orthorhombic, six-sided plates from trichloroethyleneNeedles or leaves (alcohol, aq acetone)White crystalsColorless to red, crystalline solid
용해도	less than 1 mg/mL at 68 °F (NTP, 1992)SOLUBILITY: 15 PPM IN WATER AT 100 °C. SHOWS RAPID RACEMIZATION ON ALKALI TREATMENTCRYSTALLIZES WITH SOLVENT OF CRYSTALLIZATIONCIS CONFIGURATION IS GENERALLY ACCEPTEDIn water, 15 mg/L at 100 °CSoluble in ethanol, acetone, benzeneslightly soluble in ethervery soluble in chloroformSLIGHTLY SOLUBLE IN PETROLEUM OILSSOL IN LIPIDSinsoluble in EtOHinsoluble in H2O≥77.6 mg/mL in DMSO
Corrosivity	Non-corrosive
Endocrine Disruptors	Potential endocrine disrupting compound
끓는 점	410 to 428 °F at 0.5 mmHg (NTP, 1992)BP: 215 °C at 0.5 mm Hg410-428 °FDecomposes210-220 °C/0.5 mmHg (lit.)
Decomposition	When heated to decomposition it emits acrid smoke and irritating fumes.
녹는점	159-164 °C (lit.)
굴절률	1.4593 (estimate)
저장 조건	Keep in dark place,Inert atmosphere,Room temperature
용해도	15mg l-1(100°C)
물리적 상태	흰색에서 회백색 고체
색상	White to Light yellow to Light orange
Merck	14,8271
BRN	6773081
헨리 상수	8.8×107 mol/(m3Pa) at 25℃, HSDB (2015)
안정성	안정적이지만 빛과 공기에 민감함. 타기 쉬운. 특히 알칼리가 있는 경우 산화제와 호환되지 않습니다.
InChI	1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1
InChIKey	JUVIOZPCNVVQFO-HBGVWJBISA-N
SMILES	COc1cc2OCC3Oc4c5C[C@@H](Oc5ccc4C(=O)C3c2cc1OC)C(C)=C
NIST	Rotenone(83-79-4)
EPA	Rotenone (83-79-4)

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 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).

안전 및 규제

GHS 분류	DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)H301 (97.3%): Toxic if swallowed [Danger Acute toxicity, oral]
규제 정보	Rote is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)2008/317Rotenone: HSNO Approval: HSR003076 Approved with controls
기타 안전 정보	IMAP assessments - [1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-, [2R-(2.alpha.,6a.alpha.,12a.alpha.)]-: Environment tier I assessment
운송 라벨(DOT)	Poison
화재 위험	Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992)
화재 가능성	Flammable if preheated.
건강 유해성	Excerpt from NIOSH Pocket Guide for Rotenone:
유해성 요약	Formulations for home use are classified as slightly toxic. The emulsified concentrate is classified as highly toxic. Only certified applicators can use rotenone on cranberries and for fish control. [EXTOXNET] Skin and respiratory irritation has been reported after occupational exposure. [EPA Pesticides] Poisoning by ingestion in humans may result in convulsions and coma. [ACGIH] Liver and kidney injury may occur after ingestion. [ICSC] Rotenone is used in an experimental animal model of Parkinson's syndrome, but the large doses used are not likely to be relevant to occupational exposure levels. [Reference #2] Decomposes within days when exposed to light and airNo evidence to support a causal relationship between rotenone and Parkinson's diseaseIn a fatal poisoning case, the estimated oral dose was 50 mg/kg, and the symptoms were coma and respiratory arrest within 8.5 hours of ingestion[Krieger, p. 135-41]
반응성 그룹	Ketones
EC 분류	Symbol: T, NR: 25-36/37/38-50/53

용도

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.

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).

일반 설명

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