Macelignan

Macelignan
	Chemical structure of macelignanChemical structure of macelignan
Names
	IUPAC name (8S,8′R)-3-Methoxy-3′,4′-[methylenebis(oxy)]lignan-4-ol
	Systematic IUPAC name 4-[(2S,3R)-4-(2H-1,3-Benzodioxol-5-yl)-2,3-dimethylbutyl]-2-methoxyphenol
	Other names Anwulignan
Identifiers
CAS Number	107534-93-0 ☒;
3D model (JSmol)	Interactive image;
ChemSpider	8579683 check;
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PubChem CID	10404245;
UNII	8PP3614Z43;
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	InChI InChI=1S/C20H24O4/c1-13(8-15-4-6-17(21)19(10-15)22-3)14(2)9-16-5-7-18-20(11-16)24-12-23-18/h4-7,10-11,13-14,21H,8-9,12H2,1-3H3/t13-,14+/m0/s1 ☒ Key: QDDILOVMGWUNGD-UONOGXRCSA-N ☒; InChI=1/C20H24O4/c1-13(8-15-4-6-17(21)19(10-15)22-3)14(2)9-16-5-7-18-20(11-16)24-12-23-18/h4-7,10-11,13-14,21H,8-9,12H2,1-3H3/t13-,14+/m0/s1 Key: QDDILOVMGWUNGD-UONOGXRCBH;
	SMILES C[C@H](CC1=CC2=C(C=C1)OCO2)[C@@H](C)CC3=CC(=C(C=C3)O)OC;
Properties
Chemical formula	C20H24O4
Molar mass	328.40 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ☒ verify (what is check☒ ?) Infobox references

Macelignan (Anwulignan) is a lignan. It can be found in Myristica fragrans, the nutmeg.

Medical research

One study has shown that macelignan may exert antimicrobial and anticariogenic activity against Streptococcus mutans, but this is not a currently used treatment.^[1]^[2]

Macelignan may also act as an antidiabetic molecule via PPAR signaling^[3] and upregulate adipocyte gene expression^[4]

Macelignan may contain antioxidant and anti-inflammatory properties^[5]^[4] and is marketed in breast enhancement creams for its anti-aging properties.^[6]

References

^ Dental Caries and Medicinal Plants –An Overview. B. Parimala Devi and R. Ramasubramaniaraj, Journal of Pharmacy Research 2009, 2(11),1669-1675 Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
^ Anticariogenic activity of macelignan isolated from Myristica fragrans (nutmeg) against Streptococcus mutans. J.Y. Chung, J.H. Choo, M.H. Lee and J.K. Hwang, Phytomedicine, Volume 13, Issue 4, 13 March 2006, Pages 261-266, Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
^ Therapeutic Potential of Peroxisome Proliferators–Activated Receptor-α/γ Dual Agonist With Alleviation of Endoplasmic Reticulum Stress for the Treatment of Diabetes http://diabetes.diabetesjournals.org/content/57/3/737.long
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[1] Dental Caries and Medicinal Plants –An Overview. B. Parimala Devi and R. Ramasubramaniaraj, Journal of Pharmacy Research 2009, 2(11),1669-1675 Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).

[2] Anticariogenic activity of macelignan isolated from Myristica fragrans (nutmeg) against Streptococcus mutans. J.Y. Chung, J.H. Choo, M.H. Lee and J.K. Hwang, Phytomedicine, Volume 13, Issue 4, 13 March 2006, Pages 261-266, Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).

[3] Therapeutic Potential of Peroxisome Proliferators–Activated Receptor-α/γ Dual Agonist With Alleviation of Endoplasmic Reticulum Stress for the Treatment of Diabetes http://diabetes.diabetesjournals.org/content/57/3/737.long

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v t e Types of lignans
Lignans	Arboreol Arctigenin Chamaecypanone A and B Eudesmin Globoidnan A Gmelanone Gmelinol Gummadiol Isootobanone Lyoniresinol Macelignan Matairesinol Obtulignolide Pinoresinol Pluviatilol Podophyllotoxin Secoisolariciresinol Sesamin Sesamolin Steganacin
Lignan glycosides	Arctiin Aviculin (isolariciresinol-9'-rhamnopyranoside) Secoisolariciresinol diglucoside (SDG)
Mammalian lignans (enterolignans)	Enterodiol Enterolactone Lariciresinol Hydroxymatairesinol Syringaresinol
Neolignans	Balanophonin Eusiderin Honokiol Interiotherin Linderin A Magnolol Megaphone 4-O-Methylhonokiol Rhaphidecursinol A Rhaphidecursinol B
Flavonolignans	Cinchonain-Ib Dehydrosilybin Deoxysilycistin Deoxysilydianin Hydnocarpin Hydnowightin Neosilyhermin Palstatin Rhodiolin Salcolin A Salcolin B Scutellaprostin A, B, C, D, E and F Silandrin Silyamandin Silibinin Silybinome Silicristin Silydianin Silyhermin Tricin 4'-O-(erythro-beta-guaiacylglyceryl) ether Tricin 4'-O-(threo-beta-guaiacylglyceryl) ether

Names
Chemical structure of macelignan Chemical structure of macelignan
IUPAC name (8S,8′R)-3-Methoxy-3′,4′-[methylenebis(oxy)]lignan-4-ol
Systematic IUPAC name 4-[(2S,3R)-4-(2H-1,3-Benzodioxol-5-yl)-2,3-dimethylbutyl]-2-methoxyphenol
Other names Anwulignan
Identifiers
CAS Number	107534-93-0^☒N
3D model (JSmol)	Interactive image
ChemSpider	8579683^checkY
ECHA InfoCard	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
E number	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
PubChem CID	10404245
UNII	8PP3614Z43
CompTox Dashboard (EPA)	{{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
InChI InChI=1S/C20H24O4/c1-13(8-15-4-6-17(21)19(10-15)22-3)14(2)9-16-5-7-18-20(11-16)24-12-23-18/h4-7,10-11,13-14,21H,8-9,12H2,1-3H3/t13-,14+/m0/s1^☒N Key: QDDILOVMGWUNGD-UONOGXRCSA-N^☒N InChI=1/C20H24O4/c1-13(8-15-4-6-17(21)19(10-15)22-3)14(2)9-16-5-7-18-20(11-16)24-12-23-18/h4-7,10-11,13-14,21H,8-9,12H2,1-3H3/t13-,14+/m0/s1 Key: QDDILOVMGWUNGD-UONOGXRCBH
SMILES C[C@H](CC1=CC2=C(C=C1)OCO2)[C@@H](C)CC3=CC(=C(C=C3)O)OC
Properties
Chemical formula	C₂₀H₂₄O₄
Molar mass	328.40 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ☒N verify (what is ^checkY☒N ?) Infobox references

Macelignan

Medical research

References

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