macelignan
phenol, 4-[(2S,3R)-4-(1,3-benzodioxol-5-yl)-2,3-dimethylbutyl]-2-methoxy-
 
Notes:
Constit. of Myristica fragrans (nutmeg)
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4-[(2S,3R)-4-(1,3-benzodioxol-5-yl)-2,3-dimethylbutyl]-2-methoxyphenol (Click)
CAS Number: 107534-93-0Picture of molecule
FDA UNII: 8PP3614Z43
Nikkaji Web: J1.069.117F
MDL: MFCD09953803
XlogP3-AA: 5.20 (est)
Molecular Weight: 328.40808000
Formula: C20 H24 O4
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: cosmetic agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
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US Patents: Search
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PubMed: Search
NCBI: Search
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 467.00 °C. @ 760.00 mm Hg (est)
Flash Point: 457.00 °F. TCC ( 236.20 °C. ) (est)
logP (o/w): 5.220 (est)
Soluble in:
 water, 0.06745 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:
CosIng: cosmetic data
Cosmetic Uses: antimicrobial agents
antioxidants
deodorants
oral care agents
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Suppliers:
BOC Sciences
For experimental / research use only.
Anwuligan >98%
Odor: characteristic
Use: Macelignan is a natural compound isolated from Myristica fragrans Houtt. It possesses therapeutic potentials against neurodegenerative diseases with oxidative stress and neuroinflammation.
Carbosynth
For experimental / research use only.
Anwuligan
Sigma-Aldrich: Sigma
For experimental / research use only.
Macelignan ≥98% (HPLC)
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Safety Information:
Preferred SDS: View
 
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: cosmetic agents
Recommendation for macelignan usage levels up to:
 not for fragrance use.
 
Recommendation for macelignan flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Daily Med: search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 10404245
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 4-[(2S,3R)-4-(1,3-benzodioxol-5-yl)-2,3-dimethylbutyl]-2-methoxyphenol
Chemidplus: 0107534930
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References:
 4-[(2S,3R)-4-(1,3-benzodioxol-5-yl)-2,3-dimethylbutyl]-2-methoxyphenol
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 10404245
Pubchem (sid): 135290703
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (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): HMDB36459
FooDB: FDB015348
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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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
 nutmeg seed
Search Trop  Picture
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Synonyms:
 anwulignan
(+)-anwulignan
 austrobailignan 6
4-((2S,3R)-4-(benzo[d][1,3]dioxol-5-yl)-2,3-dimethylbutyl)-2-methoxyphenol
4-[(2S,3R)-4-(1,3-benzodioxol-5-yl)-2,3-dimethylbutyl]-2-methoxyphenol
 phenol, 4-[(2S,3R)-4-(1,3-benzodioxol-5-yl)-2,3-dimethylbutyl]-2-methoxy-
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Articles:
PubMed: Glucuronidation of macelignan by human liver microsomes and expressed UGT enzymes: identification of UGT1A1 and 2B7 as the main contributing enzymes.
PubMed: Dibenzylbutane lignans from the stems of Schisandra bicolor.
PubMed: Cytotoxic and anti-tumor activities of lignans from the seeds of Vietnamese nutmeg Myristica fragrans.
PubMed: Macelignan attenuated allergic lung inflammation and airway hyper-responsiveness in murine experimental asthma.
PubMed: Multiple biological properties of macelignan and its pharmacological implications.
PubMed: Effects of macelignan isolated from Myristica fragrans (Nutmeg) on expression of matrix metalloproteinase-1 and type I procollagen in UVB-irradiated human skin fibroblasts.
PubMed: Macelignan inhibits histamine release and inflammatory mediator production in activated rat basophilic leukemia mast cells.
PubMed: Food components with anticaries activity.
PubMed: Macelignan inhibits melanosome transfer mediated by protease-activated receptor-2 in keratinocytes.
PubMed: Effect of maceligan on the systemic exposure of paclitaxel: in vitro and in vivo evaluation.
PubMed: Effects of macelignan isolated from Myristica fragrans Houtt. on UVB-induced matrix metalloproteinase-9 and cyclooxygenase-2 in HaCaT cells.
PubMed: Macelignan: a new modulator of P-glycoprotein in multidrug-resistant cancer cells.
PubMed: Macelignan attenuates activations of mitogen-activated protein kinases and nuclear factor kappa B induced by lipopolysaccharide in microglial cells.
PubMed: Machilin A isolated from Myristica fragrans stimulates osteoblast differentiation.
PubMed: Macelignan attenuates LPS-induced inflammation and reduces LPS-induced spatial learning impairments in rats.
PubMed: Determination of macelignan in rat plasma by high-performance liquid chromatography with ultraviolet detection.
PubMed: Inhibitory effects of macelignan isolated from Myristica fragrans HOUTT. on melanin biosynthesis.
PubMed: Protective Effects of macelignan on cisplatin-induced hepatotoxicity is associated with JNK activation.
PubMed: Therapeutic potential of peroxisome proliferators--activated receptor-alpha/gamma dual agonist with alleviation of endoplasmic reticulum stress for the treatment of diabetes.
PubMed: In vitro anti-biofilm activity of macelignan isolated from Myristica fragrans Houtt. against oral primary colonizer bacteria.
PubMed: Macelignan protects HepG2 cells against tert-butylhydroperoxide-induced oxidative damage.
PubMed: Anticariogenic activity of macelignan isolated from Myristica fragrans (nutmeg) against Streptococcus mutans.
PubMed: Anti-oxidant and anti-inflammatory activities of macelignan in murine hippocampal cell line and primary culture of rat microglial cells.
PubMed: Increase of caspase-3 activity by lignans from Machilus thunbergii in HL-60 cells.
PubMed: Separation of Leucas aspera, a medicinal plant of Bangladesh, guided by prostaglandin inhibitory and antioxidant activities.
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