기본 정보
- CAS
315-22-0- 표준 SMILES
CC1C(=O)OC2CCN3CC=C(COC(=O)C(C)(O)C1(C)O)C23- InChIKey
QVCMHGGNRFRMAD-UHFFFAOYSA-N- 분자식
- C16H23NO6
- 평균 분자량
- 325.36 g/mol
- 단동위원소 질량
- 325.15253745
개요
LSM-36888 is a member of pyrrolizines.
이름 및 식별자
- 우선 이름
- 4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
- IUPAC
- 5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione
- 현지명
- 모노크로탈린
- 영어명
- MONOCROTALINE
- 분자식
- C16H23NO6
- 분자량
- 325.36
이름 및 동의어
MLS00263924720-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13.alpha.,14.alpha.)-Oprea1_734543CHEMBL2134902DTXSID20859330CHEBI:125403QVCMHGGNRFRMAD-UHFFFAOYSA-N(2,3,4-gh)pyrrolizine-2,6(3H)-dione, (4,5,8,10,12,13,13a,13b)-octahydro-4,5-dihydroxy-3,4,5-trimethyl-2H-(1,6)dioxacycloundecino-LSM-368884,5-Dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dioneLS-14523SMR001548694
이름 더 보기
모노크로탈린크로탈라인CROTALINEMONOCROTALINA 6080CROTALINNSC 28693NCI-C56462Bulbus LiliiMONOCROTALINEMonccrotalireMONOCRATALINE
NS00015471Q2721598214,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione, 9CI(13-.alpha.,14-.alpha.)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione12.beta.,13.beta.-Dihydroxy-12.alpha.,13.alpha.,14.alpha.-trimethylcrotal-1-enine14,19-Dihydro-12,13-dihydroxy(13.alpha.,14.alpha.)-20-norcrotalanan-11,15-dione2H-[1,6]Dioxacycloundecino[2,3,4-gh]pyrrolizine, 20-norcrotalanan-11,15-dione deriv.4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione #
물성
구조 계산 물성
- XLogP
- -0.7
- 극성 표면적
- 96.3 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 7
- 회전 가능 결합 수
- 0
- 무거운 원자 수
- 23
- 형식 전하
- 0
- 복잡도
- 575
실험 및 물리화학적 성질
Melting Point202 - 203 °C
Physical DescriptionSolid
물리화학적 성질
- 녹는점
- 204 °C · 204 °C (dec.) (lit.)
- 끓는 점
- 463.55 °C · 463.55°C (rough estimate)
- 밀도
- 1.1512 · 1.1512 (rough estimate)
- 굴절률
- 1.55 · 1.5500 (estimate)
- 저장 조건
- 2 · 2-8°C
- 용해도
- DMSO(가온 시 최대 50mg/ml), 에탄올(가온 시 최대 10mg/ml) 또는 클로로포름(최대 50mg/ml)과 같은 유기 용매에 용해됩니다.
- 물리적 상태
- Solid
- 산도 계수 (pKa)
- 12.21 · 12.21±0.60(Predicted)
- 색상
- 하얀색
- 수용성
- 11.86 g/L · 11.86g/L(온도 미표시)
- Merck
- 13 · 13,6274
- BRN
- 48732 · 48732
- 안정성
- 1 · 제공된 대로 구매일로부터 1년 동안 안정적입니다. DMSO 또는 에탄올 용액은 -20°C에서 최대 1개월 동안 보관할 수 있습니다.
- InChI
- 1S/C16H23NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,9,11-12,20-21H,5-8H2,1-3H3/t9-,11+,12+,15+,16-/m0/s1
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
안전 데이터
- wgk
- 3
- rtecs
- QB3140000
- ridadr
- UN 1544 6.1/PG 3
- 독성
- LD50 orally in rats: 71 mg/kg (Newberne)
- HS 번호
- 29399990
- risk_code
- 25-40-35
- hazard_code
- T
- safety_code
- 36/37/39-45
- 포장분류
- III
- 위험 등급
- 6.1(b)
- Hazard Classifications
- Acute Tox. 3 OralCarc. 2
- 스토리지 클래스
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- 유해 물질 데이터
- 315-22-0(Hazardous Substances Data)
화학 및 산업
약리 정보
Cellular LocationsCytoplasm
응용 분야
개요A hepatotoxic alkaloid of the pyrrolizidine group obtained from Crotalaria retusa and C. spectabilis, the base is laevorotatory with [α]26D - 55.7° (CHCI3). It may be characterized as the hydrochloride, m.p. 184°C ldec.); [α]28D - 38.4° (H20) and the methiodide which crystallizes from MeOH with 3 moles of solvent, m.p. 205°C (dry, dec.); [α]28D + 23.4° (MeOH). Hydrolysis with boiling Ba(OHh furnishes retronecine and monocrotic acid, C7H120 3, b.p. 145-6°C/ 18 mm which is optically inactive. This acid yields a methyl ester, b.p. 94-6°Cj 18 mm, a p-bromophenacyl ester, m.p. 78°C and a 2:4-dinitrophenylhydrazone, m.p. 95-6°C. Hydrogenation in the presence of Pt02 as catalyst yields retro_x0002_necanol and monocrotalic acid, CSH120S' m.p. 181-2°C; [α]28D - 5.33° (H20) which gives a methyl ester, m.p. 79-800 C; [α]30D - 16.2° (EtOH) and a pbromophenacyl ester, m.p. 162-3°C.
역사In 1935, W.M. Neil and L.L. Russoff isolated monocrotaline from Crotalaria sessiliflora L.Monocrotaline showed anticancer activity invivo, especially for treating squamous cell carcinoma, cervical cancer, and leukemia. However, since many pyrrolizidine alkaloid compounds have hepatotoxicity, further development of these compounds is restricted.China began the research of monocrotaline, as early as 1943. Crotalaria sessiliflora L. was also recorded in the 1977 edition of the Pharmacopoeia of the People’s Republic of China. But monocrotaline was reported for its liver toxicity; teratogenic, allergic reactions; and other side effects, limiting its further clinical applications. In 1992, the Ministry of Health stopped the clinical application of monocrotaline injection. Further pharmacology study is essential for monocrotaline .
용도A toxic pyrrolizidine alkaloid isolated from Crotalaria spp. It is used for inducing pulmonary diseases in rats.
일반 설명This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG
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