| Identification | Back Directory | [Name]
(+)-LARICIRESINOL | [CAS]
27003-73-2 | [Synonyms]
Nsc329247
Lariciresil
LARICIRESINOL
Laricericinol
(+)-LARICIRESINOL
(2S)-2α-(3-Methoxy-4-hydroxyphenyl)-4β-(3-methoxy-4-hydroxybenzyl)tetrahydrofuran-3β-methanol
2α-(4-Hydroxy-3-methoxyphenyl)-3β-(hydroxymethyl)-4β-(4-hydroxy-3-methoxybenzyl)tetrahydrofuran
4-[(2S,3R,4R)-4-[(4-Hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-2-methoxyphenol
(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
(2S,3R,4R)-Tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-furanmethanol
3-Furanmethanol,tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-,(2S,3R,4R)- | [Molecular Formula]
C20H24O6 | [MDL Number]
MFCD07784476 | [MOL File]
27003-73-2.mol | [Molecular Weight]
360.4 |
| Chemical Properties | Back Directory | [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 | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
|
| Company Name: |
BioBioPha Co., Ltd. Gold
|
| Telephone: |
0871-65217109 |
| Website: |
http://www.biobiopha.com |
| Company Name: |
Sigma-Aldrich
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| Telephone: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
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