ASARININ CAS 133-04-0

Introduction：Basic information about ASARININ CAS 133-04-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

ASARININ Basic information

• Product Name: ASARININ
• Synonyms: (-)-SESAMINE;(-)-ASARININ;ASARININ;EPI-SESAMIN;(-)-5,5'-[(1R,3aα,4S,6aα)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis[1,3-benzodioxole];5,5'-[(1R,3aα,4S,6aα)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis(1,3-benzodioxole);L-Asarinin;5-[4-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-1-yl]-1,3-benzodioxole
• CAS: 133-04-0
• MF: C20H18O6
• MW: 354.35
• Product Categories: Lichen Products
• Mol File: 133-04-0.mol

ASARININ Chemical Properties

• Melting point: 121°
• alpha: D20 -118.6°; D23 -122° (chloroform)
• Boiling point: 504.4±50.0 °C(Predicted)
• density: 1.385±0.06 g/cm3(Predicted)
• storage temp.: -20°C Freezer
• solubility: Chloroform (Slightly), DMSO (Slightly, Sonicated)
• form: Solid
• color: White to Off-White
• Major Application: food and beverages
• InChI: 1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2
• InChIKey: PEYUIKBAABKQKQ-UHFFFAOYSA-N
• SMILES: O1C(C4C(C(OC4)c5cc6c(cc5)OCO6)C1)c2cc3c(cc2)OCO3

Safety Information

• WGK Germany: WGK 3
• Storage Class: 11 - Combustible Solids

ASARININ Usage And Synthesis

Description

Asarinin is a lignan that has been found in A. sieboldii. It is an epimer of sesamin and a noncompetitive inhibitor of Δ⁵-desaturase (K_i = 0.28 mM). It is selective for Δ⁵-desaturase over Δ⁶- and Δ⁹-desaturase. Asarinin is cytotoxic to A2780 and SKOV3 ovarian cancer cells (IC₅₀s = 38.45 and 60.87 μM, respectively) but not immortalized ovarian surface epithelial cells (IC₅₀ = >200 μM). It induces apoptosis and activates caspase-3, -8, and -9 in A2780 and SKOV3 cells.

Chemical Properties

White needle-like crystals, soluble in boiling methanol, ethanol, chloroform, acetone, benzene, practically insoluble in water, from A. sarum .sieboldii pepper pepper Zanthoxylum piperitum, hairy puffball Paulownia tomentosa, two-faced needle.

Uses

l-Asarinin in combination with pellitorine is a potential larvicides for the control of insecticide-resistant mosquito populations. Possesses antimicrobial activity.

in vivo

(-)-Asarinin (5-20 mg/kg; gavage; once daily; 16 weeks) improves the morphology of gastric mucosal glands, alleviate intestinal metaplasia, inhibit the STAT3 pathway, promote ROS accumulation, and induce apoptosis of gastric mucosal cells in the N-Nitroso-N-methylurea (MNU) (HY-34758)-induced mouse model of gastric precancerous lesions^[1].
(-)-Asarinin (5.0 mg/kg; oral administration; before intranasal OVA challenge) significantly inhibits the allergic reaction, reduces paw swelling and Evans blue exudation in mice, and decreases the degree of mast cell degranulation in the skin in the OVA-induced passive cutaneous anaphylaxis mouse model^[3].
(-)-Asarinin (2.50 mg/kg; oral administration) reduces the concentrations of histamine, TNF-α, MCP-1, IL-4, and IL-5 in the serum of mice in the OVA - induced systemic anaphylaxis mouse model<^[3].
(-)-Asarinin (5.0 mg/kg; oral administration; once daily; from day 21-28) significantly inhibits the scratching and sneezing responses of mice, reduces the concentrations of histamine, total IgE, and IL-4 in the serum of mice, and alleviates the inflammatory infiltration and thickening of the nasal mucosa in the OVA-induced allergic rhinitis mouse model^[3].
(-)-Asarinin (2.5 mg/kg, 5.0 mg/kg, 10 mg/kg; oral administration) inhibits paw swelling and Evans blue exudation in mice and reduces the concentrations of histamine, TNF-α, MCP-1, and IL-8 in the serum in the C48/80-induced allergic reaction mouse model^[3].
C57BL/6 mice (male, 18-22 g), OVA-induced passive cutaneous anaphylaxis model³5.0 mg/kgOral administrationSignificantly suppressed passive cutaneous anaphylaxis (PCA) in mice, reduced the degree of swelling and Evens blue exudation of mice paw, and decreased the degree of degranulation of MCs in skin.C57BL/6 mice (male, 18-22 g), OVA-induced passive cutaneous anaphylaxis model³2.50 mg/kgOral administrationSignificantly reduced the concentration of histamine, TNF-α, MCP-1, IL-4 and IL-5 in mice serum.C57BL/6 mice (male, 18-22 g), OVA-induced passive cutaneous anaphylaxis model³5.0 mg/kg Oral administration, once daily, from day 21 - 28Significantly inhibited the scratching and sneezing response of mice, reduced the concentration of histamine, total IgE, and IL - 4 in mice serum, and attenuated the inflammatory infiltrates and nasal mucosa incrassation in the AR mice.C57BL/6 mice (male, 18-22 g), C48/80-induced allergic reaction model³2.5 mg/kg, 5.0 mg/kg, 10 mg/kgOral administrationReduced C48/80-induced paw swelling and Evens blue exudation, and decreased the concentration of histamine, TNF-α, MCP-1 and IL-8 in mice serum.

• Animal Model: Animal Model: SPF-grade BALB/c mice (male and female, 18-20 g, 4-week-old), established by administration of carcinogenic agent MNU^[1]
• Dosage: 20 mg/kg, 5 mg/kg
• Administration: Gavage, once daily, 16 weeks
• Result: Reversed the deterioration of the gastric mucosal glands' morphology, reduced the severity of intestinal metaplasia, promoted ROS accumulation, inhibited the STAT3 pathway, and induced apoptosis in the gastric mucosa of GPL mice.

• Animal Model: C57BL/6 mice (male, 18-22 g), OVA-induced passive cutaneous anaphylaxis model^[3]
• Dosage: 5.0 mg/kg
• Administration: Oral administration
• Result: Significantly suppressed passive cutaneous anaphylaxis (PCA) in mice, reduced the degree of swelling and Evens blue exudation of mice paw, and decreased the degree of degranulation of MCs in skin.