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

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

RTECS 

SF7352310

HS Code 

29399990

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

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