디오스제닌
Diosgenin
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기본 정보
- CAS
512-04-9- 표준 SMILES
C[C@@H]1CC[C@@]2(OC1)O[C@H]1C[C@H]3[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C- InChIKey
WQLVFSAGQJTQCK-VKROHFNGSA-N- 분자식
- C27H42O3
- 평균 분자량
- 414.6 g/mol
- 단동위원소 질량
- 414.3133952
개요
Diosgenin is a sapogenin that is spirostan which is substituted by a hydroxy group at the 3beta position, contains a double bond at the 5-6 position, and has R- configuration at position 25. A natural product found in Dioscorea (wild yam) species, it is used as the starting point for the commercial synthesis of a number of steroids, including cortisone, pregnenolone and progesterone. It has a role as an antiviral agent, a metabolite, an antineoplastic agent and an apoptosis inducer. It is a sapogenin, a 3beta-sterol, a hexacyclic triterpenoid and a spiroketal. It derives from a hydride of a spirostan.
이름 및 식별자
- 우선 이름
- Diosgenin
- IUPAC
- (1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-ol
- 현지명
- 디오스제닌
- 영어명
- Diosgenin
- 분자식
- C27H42O3
- 분자량
- 414.63
이름 및 동의어
DIOSGENIN512-04-9Nitogenin(3beta,25R)-spirost-5-en-3-olK49P2K8WLXCHEBI:4629DTXSID00895074(25R)-spirost-5-en-3beta-diolSpirost-5-en-3-ol, (3beta,25R)-NSC-33396(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro(5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icos-18-ene-6,2'-oxane)-16-ol(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-ol
이름 더 보기
디오스제닌SAPOGENINdiosgenDIOSGENIN (3B-HYDROXY-5A-SPIROSCENE)6-Keto Diosgenin3β-Hydroxy-5-spirosteneSP 37DiosgC08898iosgeninDiosgemom
RefChem:5766DTXCID301324626208-134-3DiosgenineMFCD00016887DISOGENIN(25R)-Spirost-5-en-3beta-ol(2'R,4S,5'R,6aR,6bS,8aS,8bR,9S,11aS,12aS,12bS)-5',6a,8a,9-Tetramethyl-1,3,3',4,4',5,5',6,6a,6b,6',7,8,8a,8b,9,11a,12,12a,12b-icosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-ol
물성
구조 계산 물성보충 중
- XLogP
- 5.7
- 극성 표면적
- 38.7 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 3
- 회전 가능 결합 수
- 0
- 무거운 원자 수
- 30
- 형식 전하
- 0
- 복잡도
- 746
실험 및 물리화학적 성질
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Spirostanols and derivatives [ST0108]
SpringerMaterials PropertiesCrystal structure
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section
200.92 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
208.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
물리화학적 성질
- 녹는점
- 205 · 205-208°C
- 끓는 점
- 473.46 °C · 473.46°C (rough estimate)
- 밀도
- 1.0483 · 1.0483 (rough estimate)
- 굴절률
- 1.47 · 1.4700 (estimate)
- 저장 조건
- 2 · 2-8°C
- 용해도
- 20 mg/mL, · 클로로포름: 20mg/mL, 투명, 약간 노란색
- 산도 계수 (pKa)
- 15.02 · 15.02±0.70(Predicted)
- 물리적 상태
- 고체
- 색상
- 흰색에서 연한 노란색
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
This chemical does not meet GHS hazard criteria for 42.9% (3 of 7) of reports.
Warning
H315 (28.6%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 7 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
Regulatory InformationStatus: Active Update: 04-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/31815
Hazard Classes and CategoriesSkin Irrit. 2 (28.6%)
안전 데이터
- wgk
- 2
- rtecs
- WH1450000
- HS 번호
- 29329990
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36/37-24/25
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
응용 분야
출처Primary sources of diosgenin (a steroidal sapogenin) include Smilax China, Rhizoma polygonati, Solanum incanum, Solanum xanthocarpum, Dioscorea villosa, Trigonella foenum graecum (fenugreek), and Dioscorea Linn (wild yams). It is commercially obtained from wild yam tubers and rootstock[1-2].
용도Aglicone of saponin dioscin. Diosgenin exists in some food supplements and herbal medicines and lowers plasma cholesterol by increasing fecal cholesterol excretion. e and Progesterone.
일반 설명Diosgenin is a triterpene and a glycone derivative of dioscin. Yams, Trigonella foenum-graecum and Costus speciosus are some of its source.
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