ChemicalBook CAS DataBase List 27003-73-2

27003-73-2

Name	(+)-LARICIRESINOL
CAS	27003-73-2
Molecular Formula	C20H24O6
MDL Number	MFCD07784476
Molecular Weight	360.4
MOL File	27003-73-2.mol

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 Data

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

Hazard Information

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

Spectrum Detail

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