| Name: | 4-[(3S,3aR,6S,6aR)-6-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenol |
| CAS Number: | 1177-14-6 |  3D/inchi
|
| FDA UNII: | 155K1084GO |
| Nikkaji Web: | J15.958A |
| XlogP3-AA: | 2.20 (est) |
| Molecular Weight: | 418.44282000 |
| Formula: | C22 H26 O8 |
| BioActivity Summary: | listing |
| NMR Predictor: | Predict (works with chrome, Edge or firefox) |
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
|
| Food Chemicals Codex Listed: | No |
| Boiling Point: | 594.70 °C. @ 760.00 mm Hg (est)
|
| Flash Point: | 596.00 °F. TCC ( 313.50 °C. ) (est)
|
| logP (o/w): | 0.710 (est) |
| Soluble in: |
| | water, 88.36 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
| Alfa Biotechnology |
| For experimental / research use only. |
| Syringaresinol 98%
|
| BOC Sciences |
| For experimental / research use only. |
| Syringaresinol 0.985
Odor: characteristic Use: Syringaresinol comes from the herbs of Liriodendron tulipifera. It induces vasorelaxation by enhancing NO production in endothelial cells. And it shows inhibitory effects on the P-glycoprotein in adriamycin-resistant human breast cancer cells, MCF-7/ADR.
Liver protection; platelet aggregation inhibitors |
| Coompo |
| For experimental / research use only. |
| DL-Syringaresinol from Plants ≥96%
Odor: characteristic Use: Syringaresinol inhibits Helicobacter pylori motility.
Syringaresinol induces vasorelaxation by enhancing NO production in endothelial cells via two distinct mechanisms, phosphatidylinositol 3-kinase/Akt- and PLC/Ca(2+)/CaMKKβ -dependent eNOS phosphorylation and Ca(2+)-dependent eNOS dimerization.
Syringaresinol showed inhibitory effects on the P-glycoprotein in adriamycin-resistant human breast cancer cells, MCF-7/ADR.
(-)-Syringaresinol decreased the viability of HL-60 cells by inducing G1 arrest followed by apoptosis in a dose- and time-dependent manner. The G0/G1 phase of the cell cycle is regulated by cyclin-dependent kinases (Cdk), cyclins and cyclin-dependent kinase inhibitors (Cdki). We show by western blot analysis, that the (-)-syringaresinol-induced G1 arrest was mediated through the increased expression of Cdki proteins (p21cip1/waf1 and p27kip1) with a simultaneous decrease in cdk2, cdk4, cdk6, cyclin D1, cyclin D2, and cyclin E expression. The induction of apoptosis after treatment with (-)-syringaresinol for 24 h was demonstrated by morphological changes, DNA fragmentation, altered ratio of Bax/Bcl-2, cleavage of poly(ADP-ribose) polymerase and flow cytometry analysis. (-)-Syringaresinol also induced cytochrome c release and activation of caspase-3 and caspase-9. To our knowledge, this is the first time that (-)-syringaresinol has been reported to potently inhibit the proliferation of human promyelocytic HL-60 cells through G1 arrest and induction of apoptosis. These findings suggest that (-)-syringaresinol may be a potential chemotherapeutic agent for the treatment of cancer. |
Safety Information:
| |
| Hazards identification |
| |
| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
| |
| Pictogram | |
| |
| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
|
Not determined
|
| Dermal Toxicity: |
|
Not determined
|
| Inhalation Toxicity: |
|
Not determined
|
Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for (+)-syringaresionol usage levels up to: | | | not for fragrance use.
|
| |
| Recommendation for (+)-syringaresionol flavor usage levels up to: |
| | not for flavor use.
|
Safety References:
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :443023 |
| National Institute of Allergy and Infectious Diseases:Data |
| 4-[(3S,3aR,6S,6aR)-6-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenol |
| Chemidplus:0001177146 |
References:
| | 4-[(3S,3aR,6S,6aR)-6-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenol |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 443023 |
| Pubchem (cas): | 1177-14-6 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| 4-[(3S,3aR,6S,6aR)-6-(4- | hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenol | | | phenol, 4,4'-(tetrahydro-1H,3H-furo(3,4-c)furan-1,4-diyl)bis(2,6-dimethoxy-, (1S-(1a,3aa,4a,6aa))- | | | phenol, 4,4'-[(1S,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis[2,6-dimethoxy- | | (+)- | syringaresinol | | 4,4'-(1S,3aR,4S,6aR)- | tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diylbis(2,6-dimethoxyphenol) | | (7a,7'a,8a,8'a)-3,3',5,5'- | tetramethoxy-7,9':7',9-diepoxylignan-4,4'-diol | | (7a,7'a,8a,8'a)-3,3',5,5'- | tetramethoxy-7,9':7',9-diepoxylignane-4,4'-diol |
Articles:
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