26166-39-2

26166-39-2 structure

Name: Ascochlorin
Chemical Name: 5-chloro-2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-(1,2,6-trimethyl-3-oxocyclohexyl)penta-2,4-dienyl]benzaldehyde
CAS Number: 26166-39-2
Molecular Formula: C₂₃H₂₉ClO₄
Molecular Weight: 404.92700
Catalog: Signaling Pathways Apoptosis Apoptosis
Create Date: 2017-08-13 13:43:07
Modify Date: 2025-08-23 05:31:37
Ascochlorin (Ilicicolin D), an isoprenoid antibiotic, mediates its anti-tumor effects predominantly through the suppression of STAT3 signaling cascade. Ascochlorin induces apoptosis. Anti-inflammatory activity[1][2][3].

Name	5-chloro-2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-(1,2,6-trimethyl-3-oxocyclohexyl)penta-2,4-dienyl]benzaldehyde
Synonyms	Ascochlorin Ilicicolin D ascochlorin

Description	Ascochlorin (Ilicicolin D), an isoprenoid antibiotic, mediates its anti-tumor effects predominantly through the suppression of STAT3 signaling cascade. Ascochlorin induces apoptosis. Anti-inflammatory activity[1][2][3].
Related Catalog	Signaling Pathways >> Stem Cell/Wnt >> STAT Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Signaling Pathways >> JAK/STAT Signaling >> STAT Research Areas >> Inflammation/Immunology
Target	STAT3 Apoptosis
In Vitro	Ascochlorin (Ilicicolin D) (10-50 μM; 24-72 hours) inhibits the viability of HepG2, HCCLM3 and Huh7 cells in a time and dose dependent manner[3]. Ascochlorin (50 μM; 48 hours) induces apoptosis in HCC cells[3]. Ascochlorin (1-50 μM) significantly suppresses the production of nitric oxide (NO) and prostaglandin E2 (PGE2) and decreases the gene expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) in a dose-dependent manner. Ascochlorin inhibits the mRNA expression and the protein secretion of interleukin (IL)-1β and IL-6 but not tumor necrosis factor (TNF)-α in LPS-stimulated RAW 264.7 macrophage cells. Ascochlorin suppresses nuclear translocation and DNA binding affinity of nuclear factor-κB (NF-κB). Ascochlorin down-regulates phospho-extracellular signal-regulated kinase 1/2 (p-ERK1/2) and p-p38[2]. Cell Viability Assay[3] Cell Line: HepG2, HCCLM3, Huh7 cells Concentration: 10, 25, 50 μM Incubation Time: 24, 48, 72 hours Result: Inhibit the viability of three different HCC cell lines tested (HepG2, HCCLM3 and Huh7) in a time and dose dependent manner. Western Blot Analysis[3] Cell Line: HepG2 cells Concentration: 50 μM Incubation Time: 48 hours Result: Inhibited expression of the cell cycle regulator protein cyclin D1, the anti-apoptotic proteins Bcl-2, Mcl-1, survivin and XIAP, and the invasive gene product MMP-9.
In Vivo	Ascochlorin (Ilicicolin D) (2.5-5 mg/kg; i.p.; day 0, 1, 2, 3, 13, 15, 17, 20, 22, 24, 27, 29 and 31) inhibits tumor growth in an orthotopic HCC mouse model[1]. Animal Model: Eight week-old athymic balb/c nude female mice (HCCLM3-Luc2 tumors)[3] Dosage: 2.5 mg/kg, 5 mg/kg Administration: I.p.; day 0, 1, 2, 3, 13, 15, 17, 20, 22, 24, 27, 29 and 31 Result: Induced significant inhibition of tumor growth.
References	[1]. Min-Wen JC, et al. Molecular Targets of Ascochlorin and Its Derivatives for Cancer Therapy. Adv Protein Chem Struct Biol. 2017;108:199-225. [2]. Lee SH, et al. Anti-Inflammatory Effect of Ascochlorin in LPS-Stimulated RAW 264.7 Macrophage Cells Is Accompanied With the Down-Regulation of iNOS, COX-2 and Proinflammatory Cytokines Through NF-κB, ERK1/2, and p38 Signaling Pathway. J Cell Biochem. 2016 Apr;117(4):978-87. [3]. Dai X, et al. Ascochlorin, an isoprenoid antibiotic inhibits growth and invasion of hepatocellular carcinoma by targeting STAT3 signaling cascade through the induction of PIAS3. Mol Oncol. 2015 Apr;9(4):818-33.

Density	1.199g/cm3
Boiling Point	556.9ºC at 760mmHg
Molecular Formula	C₂₃H₂₉ClO₄
Molecular Weight	404.92700
Flash Point	290.6ºC
Exact Mass	404.17500
PSA	74.60000
LogP	5.55850
Vapour Pressure	5.2E-13mmHg at 25°C
Index of Refraction	1.603

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VH3707560

CHEMICAL NAME :: beta-Resorcylaldehyde, 5-chloro-6-methyl-3-(3-methyl-5-(1,2,6-trimethyl-3-ox ocyclohexyl)- 2,4-pentadienyl)-, (E,E)-

CAS REGISTRY NUMBER :: 26166-39-2

LAST UPDATED :: 199312

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C23-H29-Cl-O4

MOLECULAR WEIGHT :: 404.97

WISWESSER LINE NOTATION :: L6VTJ B1 C1U1Y1&U2R BQ FQ CG D1 EVH& E1 F1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 20 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 21,539,1968

RIDADR	NONH for all modes of transport

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.

26166-39-2	2550720-02-8
2877685-59-9	2877672-27-8
2877638-21-4	2877628-58-3
2877689-06-8	2138517-93-6
2877633-72-0	2759447-82-8
1880217-00-4	2137488-98-1