52659-56-0

Basic information

• Product Name: KIRENOL
• Synonyms: (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-methanol;Kirenol;KIRENOL(P);Kirel;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)-
• CAS NO: 52659-56-0
• Molecular Formula: C₂₀H₃₄O₄
• Molecular Weight: 338.48
• Product Categories: Miscellaneous Natural Products;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 52659-56-0.mol
• Article Data: 0

Chemical Properties

• Melting Point: 197.0 to 201.0 °C
• Boiling Point: 516.902 °C at 760 mmHg
• Flash Point: 233.593 °C
• Appearance: /
• Density: 1.177 g/cm³
• Refractive Index: 1.57
• Storage Temp.: -20°C Freezer
• Solubility: Ethanol (Slightly), Methanol (Slightly)
• PKA: 14.06±0.20(Predicted)
• CAS DataBase Reference: KIRENOL(CAS DataBase Reference)
• NIST Chemistry Reference: KIRENOL(52659-56-0)
• EPA Substance Registry System: KIRENOL(52659-56-0)

Safety Data

• Safety Statements: 24/25
• RTECS: SF7352310
• Hazardous Substances Data: 52659-56-0(Hazardous Substances Data)

Usage

Description

Kirenol is a diterpenoid with diverse biological activities, including anti-arthritic, anti-inflammatory, and antimicrobial properties. It has been found in S. orientalis and is known for its ability to induce apoptosis in human chronic myeloid leukemia cells.

Uses

Used in Pharmaceutical Applications:
Kirenol is used as an anti-arthritic agent for reducing the arthritis index, NF-kB activity, and paw swelling in a rat model of collagen-induced arthritis. It also increases annexin-1 expression without affecting glucocorticoid receptor α (GRα) expression in the synovium.
Kirenol is used as an anti-inflammatory agent for reducing motor deficit, delaying disease onset, and downregulating inflammatory CD4+IFN-γ+ Th1 cells and CD4+IL-17A+ Th17 cells in a mouse model of experimental autoimmune encephalomyelitis (EAE).
Kirenol is used as an antimicrobial agent for inhibiting 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 is used as an anti-cancer agent for inducing apoptosis in human chronic myeloid leukemia cells and reducing K652 chronic myeloid leukemia cell viability with a 48-hour IC50 value of 18.19 μg/ml.
Used in Topical Applications:
Kirenol is used as a topical agent for reducing edema induced by carrageenan, complete Freund's adjuvant (CFA), and formalin in rats up to 44, 67, and 65%, respectively.

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+/m1/s1

Downstream Products

• 89354-37-0 Toluene-4-sulfonic acid (1R,3S,4aS,4bR,7S,10aS)-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1,4a,7-trimethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-phenanthren-1-ylmethyl ester 
• 89354-38-1 (1R,3S,4aS,4bR,7S,10aS)-1-Benzylsulfanylmethyl-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1,4a,7-trimethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-phenanthren-3-ol