Nyasol

Nyasol
Names
	IUPAC name 4,4'-[(1Z,3R)-3-Ethenyl-1-propene-1,3-diyl]bis[phenol]
	Other names cis-Hinokiresinol; (Z)-Hinokiresinol
Identifiers
CAS Number	96895-25-9;
3D model (JSmol)	Interactive image;
PubChem CID	6915833;
UNII	LK6CH9D7UR;
CompTox Dashboard (EPA)	DTXSID501337053 ;
	InChI InChI=1S/C17H16O2/c1-2-14(15-7-11-17(19)12-8-15)6-3-13-4-9-16(18)10-5-13/h2-12,14,18-19H,1H2/b6-3-/t14-/m1/s1 Key: VEAUNWQYYMXIRB-JHAQOBCDSA-N;
	SMILES C=C[C@H](/C=C\C1=CC=C(C=C1)O)C2=CC=C(C=C2)O;
Properties
Chemical formula	C17H16O2
Molar mass	252.313 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Nyasol, also known as cis-hinokiresinol or as (Z)-hinokiresinol, is a lignan that is found in Anemarrhena asphodeloides.^[1]^[2]^[3]^[4] It has estrogenic activity, acting as a selective agonist of the ERβ,^[5] and hence is a phytoestrogen.^[6]^[7]^[4] In addition, (-)-nyasol has been found to inhibit the production of eicosanoids and nitric oxide in vitro and shows anti-inflammatory effects.^[8]

References

^ J. Buckingham (1986). Dictionary of Organic Compounds. CRC Press. pp. 3544–. ISBN 978-0-412-54090-5.
^ Atta-ur-Rahman (8 July 2003). Studies in Natural Products Chemistry: Bioactive Natural Products. Elsevier. pp. 234–. ISBN 978-0-08-054205-8.
^ Christophe Wiart (11 May 2012). Medicinal Plants of China, Korea, and Japan: Bioresources for Tomorrow's Drugs and Cosmetics. CRC Press. pp. 135–. ISBN 978-1-4398-9912-0.
^ ^a ^b Kwon, J., Kondaji, G., Song, S., Kim, C., Lee, K., Kim, W. K., & Choi, Y. (2013). Synthesis of naturally occurring norlignan (±)-nyasol. Bulletin of the Korean Chemical Society, 34(4), 1247-1249.
^ Yang, H; Baggett, S; Staub, R; Chow, S; Bjeldanes, LF; Leitman, D; Cohen, I (2008). "Norlignans from Anemarrhenae asphoeloides Displaying Selective Estrogen Beta (ER?) Activity". Planta Medica. 74 (3). doi:10.1055/s-2008-1075274. ISSN 0032-0943.
^ Atta-ur- Rahman; Allen B. Reitz (1 January 2005). Frontiers in Medicinal Chemistry. Bentham Science Publishers. pp. 205–. ISBN 978-1-60805-205-9.
^ Minami E, Taki M, Takaishi S, Iijima Y, Tsutsumi S, Akiyama T (2000). "Stereochemistry of cis- and trans-hinokiresinol and their estrogen-like activity". Chem. Pharm. Bull. 48 (3): 389–92. doi:10.1248/cpb.48.389. PMID 10726863.
^ Lim H, Nam JW, Seo EK, Kim YS, Kim HP (2009). "(-)-Nyasol (cis-hinokiresinol), a norneolignan from the rhizomes of Anemarrhena asphodeloides, is a broad spectrum inhibitor of eicosanoid and nitric oxide production". Arch. Pharm. Res. 32 (11): 1509–14. doi:10.1007/s12272-009-2102-4. PMID 20091263. S2CID 23151318.

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[Buckingham1986-1] J. Buckingham (1986). Dictionary of Organic Compounds. CRC Press. pp. 3544–. ISBN 978-0-412-54090-5.

[Atta-ur-Rahman2003-2] Atta-ur-Rahman (8 July 2003). Studies in Natural Products Chemistry: Bioactive Natural Products. Elsevier. pp. 234–. ISBN 978-0-08-054205-8.

[Wiart2012-3] Christophe Wiart (11 May 2012). Medicinal Plants of China, Korea, and Japan: Bioresources for Tomorrow's Drugs and Cosmetics. CRC Press. pp. 135–. ISBN 978-1-4398-9912-0.

[KwonKondaji2013-4] Kwon, J., Kondaji, G., Song, S., Kim, C., Lee, K., Kim, W. K., & Choi, Y. (2013). Synthesis of naturally occurring norlignan (±)-nyasol. Bulletin of the Korean Chemical Society, 34(4), 1247-1249.

[YangBaggett2008-5] Yang, H; Baggett, S; Staub, R; Chow, S; Bjeldanes, LF; Leitman, D; Cohen, I (2008). "Norlignans from Anemarrhenae asphoeloides Displaying Selective Estrogen Beta (ER?) Activity". Planta Medica. 74 (3). doi:10.1055/s-2008-1075274. ISSN 0032-0943.

[RahmanReitz2005-6] Atta-ur- Rahman; Allen B. Reitz (1 January 2005). Frontiers in Medicinal Chemistry. Bentham Science Publishers. pp. 205–. ISBN 978-1-60805-205-9.

[pmid10726863-7] Minami E, Taki M, Takaishi S, Iijima Y, Tsutsumi S, Akiyama T (2000). "Stereochemistry of cis- and trans-hinokiresinol and their estrogen-like activity". Chem. Pharm. Bull. 48 (3): 389–92. doi:10.1248/cpb.48.389. PMID 10726863.

[pmid20091263-8] Lim H, Nam JW, Seo EK, Kim YS, Kim HP (2009). "(-)-Nyasol (cis-hinokiresinol), a norneolignan from the rhizomes of Anemarrhena asphodeloides, is a broad spectrum inhibitor of eicosanoid and nitric oxide production". Arch. Pharm. Res. 32 (11): 1509–14. doi:10.1007/s12272-009-2102-4. PMID 20091263. S2CID 23151318.

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Names

IUPAC name 4,4'-[(1Z,3R)-3-Ethenyl-1-propene-1,3-diyl]bis[phenol]
Other names cis-Hinokiresinol; (Z)-Hinokiresinol
Identifiers
CAS Number	96895-25-9
3D model (JSmol)	Interactive image
PubChem CID	6915833
UNII	LK6CH9D7UR
CompTox Dashboard (EPA)	DTXSID501337053
InChI InChI=1S/C17H16O2/c1-2-14(15-7-11-17(19)12-8-15)6-3-13-4-9-16(18)10-5-13/h2-12,14,18-19H,1H2/b6-3-/t14-/m1/s1 Key: VEAUNWQYYMXIRB-JHAQOBCDSA-N
SMILES C=C[C@H](/C=C\C1=CC=C(C=C1)O)C2=CC=C(C=C2)O
Properties
Chemical formula	C₁₇H₁₆O₂
Molar mass	252.313 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references