(15R)-5beta,9alpha,13alpha-Ros-8(14)-ene-2beta,15,16,18-tetrol
Grundinformationen
- CAS
52659-56-0- Standard-SMILES
C[C@@]1(CO)C[C@@H](O)C[C@@H]2[C@@H]1CCC1=C[C@@](C)([C@@H](O)CO)CC[C@@]12C- InChIKey
MWHBZBYJEPTBBI-DSWGTCOTSA-N- Summenformel
- C20H34O4
- Durchschnittliche Molmasse
- 338,5 g/mol
- Monoisotopische Masse
- 338,24570956
Namen und Bezeichner
- Bevorzugter Name
- (15R)-5beta,9alpha,13alpha-Ros-8(14)-ene-2beta,15,16,18-tetrol
- IUPAC
- (1R)-1-[(2S,4aR,4bR,6S,8R,8aS)-6-hydroxy-8-(hydroxymethyl)-2,4a,8-trimethyl-4,4b,5,6,7,8a,9,10-octahydro-3H-phenanthren-2-yl]ethane-1,2-diol
- Englischer Name
- KIRENOL
- Summenformel
- C20H34O4
- Molmasse
- 338.49
Namen und Synonyme
DTXSID60856141(15R)-5beta,9alpha,13alpha-Ros-8(14)-ene-2beta,15,16,18-tetrol(2beta,5beta,9alpha,13alpha,15R)-Ros-8(14)-ene-2,15,16,18-tetrolKirelKirenolKIRENOL(P)Kirenol (Standard)Kirenol, 10 mM in DMSO(1R)-1-[(2S,4aR,4bS,6S,8R,8aS)-6-hydroxy-8-(hydroxymethyl)-2,4b,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-2-yl]ethane-1,2-diol(1R,3S,4aS,4bS,7S,10aS)-1,2,3,4,4a,4b,5,6,7,9,10,10a-Dodecahydro-3-hydroxy-7-[(R)-1,2-dihydroxyethyl]-1,4a,7-trimethylphenanthrene-1-methanol1,7-Phenanthrenedimethanol, 1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-3-hydroxy-α7-(hydroxymethyl)-1,4a,7-trimethyl-, (α7R,1R,3S,4aS,4bR,7S,10aS)-(R)-1-((2S,4aR,4bS,6S,8R,8aS)-6-Hydroxy-8-(hydroxymethyl)-2,4b,8-trimethyl-2,3,4,4a,4b,5,6,7,8,8a,9,10-dodecahydrophenanthren-2-yl)ethane-1,2-diol
Weitere Namen anzeigen
1,7-PhenanthrenediMethanol,1,2,3,4,4a,4b,5,6,7,- 9,10,10a-dodecahydro-3-hydroxy-R7- (hydroxyMethyl)-1,4a,7-triMethyl-,(R7R,1R,- 3S,4aS,4bR,7S,10aS)-
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,1
- Polarare Oberfläche (TPSA)
- 80,9 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 24
- Formalladung
- 0
- Komplexität
- 518
Physikochemische Eigenschaften
- Schmelzpunkt
- 197 to · 197.0 to 201.0 °C
- Siedepunkt
- 516.9 · 516.9±35.0 °C(Predicted)
- Dichte
- 1.17 · 1.17±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer
- Löslichkeit
- Ethanol (Slightly), Methanol (Slightly)
- Aggregatzustand
- Solid
- pka
- 14.06 · 14.06±0.20(Predicted)
- Farbe
- White to Light Yellow
- Major Application
- food and beverages
- Kosmetik-Inhaltsstoffe Funktionen
- ANTIMICROBIALHAIR CONDITIONINGSKIN CONDITIONING - EMOLLIENTANTIOXIDANT
- InChI
- InChI=1/C20H34O4/c1-18(17(24)11-21)7-6-15-13(8-18)4-5-16-19(2,12-22)9-14(23)10-20(15,16)3/h8,14-17,21-24H,4-7,9-12H2,1-3H3/t14-,15-,16-,17+,18+,19+,20+/s3
- InChIKey
- NRYNTARIOIRWAB-QNOIMPALNA-N
- SMILES
- C[C@@]12C[C@H](O)C[C@@](C)(CO)[C@@]1([H])CCC1=C[C@@](C)([C@@H](O)CO)CC[C@@]21[H] |&1:1,3,6,10,16,18,24,r|
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- WGK 3
- hs_code
- 29399990
- RTECS-Nr.
- SF7352310
- safety_code
- 24/25
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Anwendungen
BeschreibungKirenol is a diterpenoid that has been found in S. orientalis and has diverse biological activities, including anti-arthritic and anti-inflammatory properties. It inhibits Gram-positive and Gram-negative bacterial growth in disc diffusion assays with MICs ranging from 39 to 156 and 312.5 to 625 μg/ml, respectively. Kirenol also reduces K652 chronic myeloid leukemia cell viability with a 48 hour IC50 value of 18.19 μg/ml and induces apoptosis. In vivo, kirenol (2 mg/kg, p.o.) reduces motor deficit, delays disease onset by approximately five days, and downregulates inflammatory CD4+IFN-γ+ Th1 cells and CD4+IL-17A+ Th17 cells in a mouse model of experimental autoimmune encephalomyelitis (EAE). Intragastric administration of kirenol (1-4 mg/kg) reduces the arthritis index, NF-kB activity, and paw swelling and increases annexin-1 expression without affecting glucocorticoid receptor α (GRα) expression in the synovium in a rat model of collagen-induced arthritis. Topical administration of kirenol (0.3-0.5% w/w) reduces edema induced by carrageenan, complete Freund''s adjuvant (CFA), and formalin in rats up to 44, 67, and 65%, respectively.
VerwendenKirenol is a pharmaceutical agent that induces apoptosis in human chronic myeloid leukemia cells.
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