KIRENOL CAS 52659-56-0

Introduction：Basic information about KIRENOL CAS 52659-56-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

KIRENOL 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)-;1,7-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)-;(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;KirenolQ: What is Kirenol Q: What is the CAS Number of Kirenol Q: What is the storage condition of Kirenol Q: What are the applications of Kirenol
• CAS: 52659-56-0
• MF: C20H34O4
• MW: 338.49
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Miscellaneous Natural Products
• Mol File: 52659-56-0.mol

KIRENOL Chemical Properties

• Melting point: 197.0 to 201.0 °C
• Boiling point: 516.9±35.0 °C(Predicted)
• density: 1.17±0.1 g/cm3(Predicted)
• storage temp.: -20°C Freezer
• solubility: Ethanol (Slightly), Methanol (Slightly)
• form: Solid
• pka: 14.06±0.20(Predicted)
• color: White to Light Yellow
• Major Application: food and beverages
• Cosmetics Ingredients Functions: ANTIMICROBIAL HAIR CONDITIONING SKIN CONDITIONING - EMOLLIENT ANTIOXIDANT
• 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|
• CAS DataBase Reference: 52659-56-0

Safety Information

• Safety Statements: 24/25
• WGK Germany: WGK 3
• RTECS: SF7352310
• HS Code: 29399990
• Storage Class: 11 - Combustible Solids

KIRENOL Usage And Synthesis

Description

Kirenol 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.

Chemical Properties

Yellow crystalline powder, easily soluble in methanol, poorly soluble in water, derived from Siegesbeckia serrata.

Uses

Kirenol is a pharmaceutical agent that induces apoptosis in human chronic myeloid leukemia cells.

Definition

ChEBI: Kirenol is a diterpenoid.

References

[1] ZHE-MING WANG . Kirenol upregulates nuclear Annexin-1 which interacts with NF-κB to attenuate synovial inflammation of collagen-induced arthritis in rats[J]. Journal of ethnopharmacology, 2011, 137 1: Pages 774-782. DOI: 10.1016/j.jep.2011.06.037
[2] JIAN-PING WANG . Topical anti-inflammatory and analgesic activity of kirenol isolated from Siegesbeckia orientalis[J]. Journal of ethnopharmacology, 2011, 137 3: Pages 1089-1094. DOI: 10.1016/j.jep.2011.07.016
[3] JIAN-PING WANG  Yong H Z  Ya Ming Zhou. Kirenol production in hairy root culture of Siegesbeckea orientalis and its antimicrobial activity.[J]. Pharmacognosy Magazine, 2012, 8 30: 149-155. DOI: 10.4103/0973-1296.96569
[4] YUE LU. Kirenol, a compound from Herba Siegesbeckiae, induces apoptosis in human chronic myeloid leukemia K562 cells.[J]. Pharmazie, 2014, 69 2: 148-153.
[5] JUAN XIAO. Kirenol attenuates experimental autoimmune encephalomyelitis by inhibiting differentiation of Th1 and th17 cells and inducing apoptosis of effector T cells.[J]. Scientific Reports, 2015: 9022. DOI: 10.1038/srep09022