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66322-34-7 | Dihydroguaiaretic acid
CAS No: 66322-34-7 Catalog No: AG00393X MDL No:MFCD02752706
Product Description
Catalog Number:
AG00393X
Chemical Name:
Dihydroguaiaretic acid
CAS Number:
66322-34-7
Molecular Formula:
C20H26O4
Molecular Weight:
330.4180
MDL Number:
MFCD02752706
IUPAC Name:
4-[(2S,3R)-4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl]-2-methoxyphenol
InChI:
InChI=1S/C20H26O4/c1-13(9-15-5-7-17(21)19(11-15)23-3)14(2)10-16-6-8-18(22)20(12-16)24-4/h5-8,11-14,21-22H,9-10H2,1-4H3/t13-,14+
InChI Key:
ADFOLUXMYYCTRR-OKILXGFUSA-N
SMILES:
COc1cc(ccc1O)C[C@H]([C@H](Cc1ccc(c(c1)OC)O)C)C
UNII:
S81Z40PSJ4
Properties
Complexity:
328
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
2
Defined Bond Stereocenter Count:
0
Exact Mass:
330.183g/mol
Formal Charge:
0
Heavy Atom Count:
24
Hydrogen Bond Acceptor Count:
4
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
330.424g/mol
Monoisotopic Mass:
330.183g/mol
Rotatable Bond Count:
7
Topological Polar Surface Area:
58.9A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
5
Literature
| Title | Journal |
|---|---|
| Antibacterial and antimycobacterial lignans and flavonoids from Larrea tridentata. | Phytotherapy research : PTR 20121201 |
| Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases. | Journal of medicinal chemistry 20110324 |
| Larvicidal activity of (-)-dihydroguaiaretic acid derivatives against Culex pipiens. | Bioscience, biotechnology, and biochemistry 20110101 |
| meso-Dihydroguaiaretic acid inhibits hepatic lipid accumulation by activating AMP-activated protein kinase in human HepG2 cells. | Biological & pharmaceutical bulletin 20110101 |
| [Effective components against HIV-1 replicative enzymes isolated from plants]. | Yao xue xue bao = Acta pharmaceutica Sinica 20100201 |
| Chemical constituents of the bark of Machilus wangchiana and their biological activities. | Journal of natural products 20091201 |
| Antimicrobial activity of stereoisomers of butane-type lignans. | Bioscience, biotechnology, and biochemistry 20090801 |
| Lignans with anti-HIV activity from Schisandra propinqua var. sinensis. | Journal of natural products 20090601 |
| 2,2'-Dimethoxy-4,4'-[rel-(2R,3S)-2,3-di-methylbutane-1,4-diyl]diphenol. | Acta crystallographica. Section E, Structure reports online 20090601 |
| Isolation, structure elucidation and cytotoxic evaluation of endiandrin B from the Australian rainforest plant Endiandra anthropophagorum. | Bioorganic & medicinal chemistry 20090201 |
| Antioxidant activity of butane type lignans, secoisolariciresinol, dihydroguaiaretic acid, and 7,7'-oxodihydroguaiaretic acid. | Bioscience, biotechnology, and biochemistry 20081101 |
| Meso-dihydroguaiaretic acid isolated from Saururus chinensis inhibits cyclooxygenase-2 and 5-lipoxygenase in mouse bone marrow-derived mast cells. | Archives of pharmacal research 20080501 |
| Low-density lipoprotein (LDL)-antioxidant lignans from Myristica fragrans seeds. | Bioorganic & medicinal chemistry letters 20080101 |
| Isolation and antifungal activity of lignans from Myristica fragrans against various plant pathogenic fungi. | Pest management science 20070901 |
| Regulation of apoptosis in eicosapentaenoic acid-treated HL-60 cells. | The Journal of surgical research 20070101 |
| Compounds with DNA cleaving activity from Kadsura ananosma. | Die Pharmazie 20061001 |
| Inhibition of protein tyrosine phosphatase 1B by lignans from Myristica fragrans. | Phytotherapy research : PTR 20060801 |
| Effect of meso-dihydroguaiaretic acid from Machilus thunbergii Sieb et Zucc on MMP-1 expression in heat shock-induced cultured primary human fibroblasts. | Phytotherapy research : PTR 20060801 |
| meso-Dihydroguaiaretic acid attenuates the neurotoxic effect of staurosporine in primary rat cortical cultures. | Neuropharmacology 20060501 |
| Microsphere-based protease assays and screening application for lethal factor and factor Xa. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501 |
| Meso-dihydroguaiaretic acid and licarin A of Machilus thunbergii protect against glutamate-induced toxicity in primary cultures of a rat cortical cells. | British journal of pharmacology 20051101 |
| Meso-dihydroguaiaretic acid from Machilus thunbergii SIEB et ZUCC., and its effects on the expression of matrix metalloproteinase-2, 9 cause by ultraviolet irradiated cultured human keratinocyte cells (HaCaT). | Biological & pharmaceutical bulletin 20051101 |
| meso-dihydroguaiaretic acid from Machilus thunbergii down-regulates TGF-beta1 gene expression in activated hepatic stellate cells via inhibition of AP-1 activity. | Planta medica 20050501 |
| Antiproliferative, anti-aromatase, anti-17beta-HSD and antioxidant activities of lignans isolated from Myristica argentea. | Planta medica 20011101 |
| Antiviral activities of methylated nordihydroguaiaretic acids. 1. Synthesis, structure identification, and inhibition of tat-regulated HIV transactivation. | Journal of medicinal chemistry 19980730 |
| Effects of n-tritriacontane-16,18-dione, curcumin, chlorphyllin, dihydroguaiaretic acid, tannic acid and phytic acid on the initiation stage in a rat multi-organ carcinogenesis model. | Cancer letters 19970226 |
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