DL-Syringaresinol

Names

[ Name ]:
DL-Syringaresinol

[Synonym ]:
syringaresinol
Phenol, 4,4'-[(1R,3aS,4R,6aS)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis[2,6-dimethoxy-
4,4'-(1S,3aR,4S,6aR)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diylbis(2,6-dimethoxyphenol)
Phenol, 4,4'-[(1S,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis[2,6-dimethoxy-
4,4'-(1R,3aS,4R,6aS)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diylbis(2,6-dimethoxyphenol)

Biological Activity

[Description]:

DL-Syringaresinol ((±)-Syringaresinol), a lignin, inhibits UVA-induced upregulation of MMP-1 by suppressing MAPK/AP-1 signaling in human HaCaT keratinocytes and dermal fibroblasts (HDFs). DL-Syringaresinol has antiphotoaging properties against UVA-induced skin aging. DL-Syringaresinol exhibits weak antimycobacterial activity against Mycobacterium tuberculosis H37Rv[1][2].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> MAPK/ERK Pathway >> p38 MAPK

Signaling Pathways >> Anti-infection >> Bacterial

[References]

[1]. Su-Yen Chang, et al. Antimycobacterial butanolides from the root of Lindera akoensis. Chem Biodivers. 2008 Dec;5(12):2690-8.

[2]. Jung Hwan Oh, et al. Syringaresinol Inhibits UVA-Induced MMP-1 Expression by Suppression of MAPK/AP-1 Signaling in HaCaT Keratinocytes and Human Dermal Fibroblasts. Int J Mol Sci. 2020 Jun 1;21(11):3981.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
594.7±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₂H₂₆O₈

[ Molecular Weight ]:
418.437

[ Flash Point ]:
313.5±30.1 °C

[ Exact Mass ]:
418.162781

[ PSA ]:
95.84000

[ LogP ]:
0.71

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.578

Safety Information

[ Hazard Codes ]:
Xi

Related Compounds

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