(+)-LARICIRESINOL CAS 27003-73-2

Introduction：Basic information about (+)-LARICIRESINOL CAS 27003-73-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

(+)-LARICIRESINOL Basic information

• Product Name: (+)-LARICIRESINOL
• Synonyms: (2S)-2α-(3-Methoxy-4-hydroxyphenyl)-4β-(3-methoxy-4-hydroxybenzyl)tetrahydrofuran-3β-methanol;(2S)-Tetrahydro-2α-(4-hydroxy-3-methoxyphenyl)-4β-[(4-hydroxy-3-methoxyphenyl)methyl]-3β-furanmethanol;2-Methoxy-4-[[(2S)-tetrahydro-2α-(3-methoxy-4-hydroxyphenyl)-3β-(hydroxymethyl)furan-4β-yl]methyl]phenol;2α-(4-Hydroxy-3-methoxyphenyl)-3β-(hydroxymethyl)-4β-(4-hydroxy-3-methoxybenzyl)tetrahydrofuran;Laricericinol;Nsc329247;Lariciresil;(+)-LARICIRESINOL
• CAS: 27003-73-2
• MF: C20H24O6
• MW: 360.4
• Product Categories: Miscellaneous Natural Products
• Mol File: 27003-73-2.mol

(+)-LARICIRESINOL Chemical Properties

• Melting point: 167-168 °C
• Boiling point: 568.4±50.0 °C(Predicted)
• density: 1.261±0.06 g/cm3(Predicted)
• storage temp.: Sealed in dry,Room Temperature
• solubility: Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
• form: Powder
• pka: 9.91±0.35(Predicted)
• color: White to off-white
• BRN: 4560057
• Major Application: metabolomics vitamins, nutraceuticals, and natural products
• InChI: InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m0/s1
• InChIKey: MHXCIKYXNYCMHY-AUSJPIAWSA-N
• SMILES: O1C[C@H](CC2=CC=C(O)C(OC)=C2)[C@H](CO)[C@H]1C1=CC=C(O)C(OC)=C1
• LogP: 1.640 (est)

Safety Information

• Hazard Codes: N
• Risk Statements: 50
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Aquatic Acute 1

(+)-LARICIRESINOL Usage And Synthesis

Uses

(+)-Lariciresinol is used in biological studies as an anti-tumor-initiating effects of phenolic compounds isolated from the bark of Picea jezoensis var. jezoensis to evaluate the pharmacological activity.

Definition

ChEBI: (+)-lariciresinol is a lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2S,3R,4R-diastereomer). It has a role as an antifungal agent and a plant metabolite. It is a member of oxolanes, a member of phenols, a lignan, a primary alcohol and an aromatic ether. It is an enantiomer of a (-)-lariciresinol.

Biological Activity

Lariciresinol is a potent dietary antioxidant and a radical scavenger by potentially chelating catalytic Fe2+ ions. It exerts antimicrobial effects against foodborne pathogens S. aureus and E. coli O157:H7. Lariciresinol is an effective anticancer agent th at inhibits cell proliferation and induces apoptosis in human HepG2 cells in vitro. It also displays anti-inflammatory and anti-diabetic effects in vitro and in vivo studies respectively.

in vivo

Lariciresinol (10 mg/kg, p.o., 3 weeks) displays anti-diabetic activity in Streptozotocin (HY-13753)-treated diabetic mice^[6].
Lariciresinol (10-30 mg/kg, i.p., 28 days) inhibits complete Freund's adjuvant-induced arthritis in rats by regulating TGF-β and NF-κB pathways^[7].
Lariciresinol (3-15 mg/kg body weight, p.o., daily, 9 weeks (tumor bearing rats); 20-100 ppm, diet, p.o., 5 weeks (E2-maintained ovariectomized athymic mice bearing orthotopic MCF-7 tumors)) inhibits tumor growth and tumor angiogenesis in mammary tumor bearing rats and E2-maintained ovariectomized athymic mice bearing orthotopic MCF-7 tumors^[8].

• Animal Model: Streptozotocin (HY-13753)-treated diabetic mice^[6]
• Dosage: 10 mg/kg
• Administration: Oral gavage (p.o.), 3 weeks
• Result: Decreased blood glucose levels and increased insulin levels. Improved pancreatic islet size, increased GLUT4 expression. Enhanced insulin signaling in skeletal muscle.

target

VEGFR | Antifection