nectandrin-B
malabaricanol
 
Notes:
None found
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CAS Number: 74683-16-2Picture of molecule3D/inchi
Other: 951322-15-9
Nikkaji Web: J259.868J
XlogP3-AA: 3.70 (est)
Molecular Weight: 344.40728000
Formula: C20 H24 O5
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 water, 4.369 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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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
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for nectandrin-B usage levels up to:
 not for fragrance use.
 
Recommendation for nectandrin-B flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 156517
National Institute of Allergy and Infectious Diseases: Data
 4-[(2R,3R,4S,5S)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol
Chemidplus: 0074683162
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References:
 4-[(2R,3R,4S,5S)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 156517
Pubchem (cas): 74683-16-2
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEMBL: View
HMDB (The Human Metabolome Database): Search
FooDB: FDB012471
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
EFSA Update of results on the monitoring of furan levels in food: Read Report
EFSA Previous report: Results on the monitoring of furan levels in food: Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food: Read Report
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 myristica fragrans
Search Trop  Picture
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Synonyms:
 calophyllin
4-[(2R,3R,4S,5S)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol
 malabaricanol
 nectandrin B
 phenol, 4,4'-((2R,3R,4S,5S)-tetrahydro-3,4-dimethyl-2,5-furandiyl)bis(2-methoxy-, rel-
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Articles:
PubMed: Degranulation inhibitors from the arils of Myristica fragrans in antigen-stimulated rat basophilic leukemia cells.
PubMed: Bioactivity-Guided Investigation of the Anti-Inflammatory Activity of Hippophae rhamnoides Fruits.
PubMed: Lignans from guaiac resin decrease nitric oxide production in interleukin 1β-treated hepatocytes.
PubMed: Hepatocyte-protective effect of nectandrin B, a nutmeg lignan, against oxidative stress: Role of Nrf2 activation through ERK phosphorylation and AMPK-dependent inhibition of GSK-3β.
PubMed: Neolignans from the Arils of Myristica fragrans as Potent Antagonists of CC Chemokine Receptor 3.
PubMed: The Blood-Brain Barrier Permeability of Lignans and Malabaricones from the Seeds of Myristica fragrans in the MDCK-pHaMDR Cell Monolayer Model.
PubMed: Nectandrin B, a lignan isolated from nutmeg, inhibits liver X receptor-α-induced hepatic lipogenesis through AMP-activated protein kinase activation.
PubMed: Nectandrin B suppresses the expression of adhesion molecules in endothelial cells: Role of AMP-activated protein kinase activation.
PubMed: [Lignans from Machilus robusta].
PubMed: Cytotoxic and anti-tumor activities of lignans from the seeds of Vietnamese nutmeg Myristica fragrans.
PubMed: Glycosides from the bark of Machilus robusta.
PubMed: Protective effect of nectandrin B, a potent AMPK activator on neointima formation: inhibition of Pin1 expression through AMPK activation.
PubMed: [Chemical constituents from roots of Machilus yaoshansis].
PubMed: Nectandrin B activates endothelial nitric-oxide synthase phosphorylation in endothelial cells: role of the AMP-activated protein kinase/estrogen receptor α/phosphatidylinositol 3-kinase/Akt pathway.
PubMed: Neuroprotective effects of constituents of Eragrostis ferruginea against Aβ-induced toxicity in PC12 cells.
PubMed: AMP-activated protein kinase (AMPK) activators from Myristica fragrans (nutmeg) and their anti-obesity effect.
PubMed: Inhibition of DNA topoisomerases I and II and cytotoxicity by lignans from Saururus chinensis.
PubMed: Machilin A isolated from Myristica fragrans stimulates osteoblast differentiation.
PubMed: In vitro antileishmanial and antimalarial activities of tetrahydrofuran lignans isolated from Nectandra megapotamica (Lauraceae).
PubMed: Protective effect of lignans against sepsis from the roots of Saururus chinensis.
PubMed: Isolation and antifungal activity of lignans from Myristica fragrans against various plant pathogenic fungi.
PubMed: Endiandrin A, a potent glucocorticoid receptor binder isolated from the Australian plant Endiandra anthropophagorum.
PubMed: Neuroprotective effects of 2,5-diaryl-3,4-dimethyltetrahydrofuran neolignans.
PubMed: Increase of caspase-3 activity by lignans from Machilus thunbergii in HL-60 cells.
PubMed: Lignans from the bark of Machilus thunbergii and their DNA topoisomerases I and II inhibition and cytotoxicity.
PubMed: Melanin biosynthesis inhibitors from the bark of Machilus thunbergii.
PubMed: Separation of Leucas aspera, a medicinal plant of Bangladesh, guided by prostaglandin inhibitory and antioxidant activities.
PubMed: Antiproliferative, anti-aromatase, anti-17beta-HSD and antioxidant activities of lignans isolated from Myristica argentea.
PubMed: Chemical constituents of two Chinese Magnoliaceae plants, Tsoongiodendron odorum and Manglietiastrum sinicum, and their inhibition of platelet aggregation.
PubMed: O-demethylation of 7,7'-epoxylignans by Aspergillus niger.
PubMed: Antitumor plants. X. Constituents of Nectandra rigida.
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