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Nordihydroguaiaretic Acid - 10mM in DMSO, high purity , CAS No.500-38-9

6 Citations COA COA
  • Cas Number:  500-38-9
  • Molecular Weight:  302.37
  • Beilstein Registry Number:   6(1)577
  • PubChem CID: 4534
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Item Number
N424310
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N424310-1ml
1ml
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$69.90
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Naturally occurring potent antioxidant

View related series
Autophagy (1917) Compound libraries (12325) Ferroptosis (356) Lipid metabolism (1912)

Basic Description

Synonyms NORDIHYDROGUAIARETIC ACID | 500-38-9 | NDGA | Dihydronorguaiaretic acid | Actinex | 4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol | Norhydroguaiaretic acid | Norguaiaretic acid, dihydro- | 1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis- | Dinorguaia
Specifications & Purity Moligand™, 10mM in DMSO
Biochemical and Physiological Mechanisms Lipoxygenase inhibitor; polyphenol-bearing o-dihydroxy (catechol) structure.Naturally occurring potent antioxidant. Various pharmacological effects in vitro and in vivo . Anticancer, antimicrobial, anti-inflammatory and immunosuppressive activities.
Storage Temp Store at -80°C
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Grade Moligand™
Product Description

Product Introduction

Nordihydroguaiaretic acid (NDGA) is used as an antioxidant and potent scavenger of reactive oxygen species (ROS)

Application

Nordihydroguaiaretic acid can be used:

In the synthesis of nordihydroguaiaretic acid derivatives with potent HIV inhibition activity；As a starting material in the synthesis of tetra-O-methylnordihydroguaiaretic  acid.

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
Superclass Lignans, neolignans and related compounds
Class Dibenzylbutane lignans
Subclass Not available
Intermediate Tree Nodes Not available
Direct Parent Dibenzylbutane lignans
Alternative Parents Phenylpropanes  Catechols  1-hydroxy-4-unsubstituted benzenoids  1-hydroxy-2-unsubstituted benzenoids  Organooxygen compounds  Hydrocarbon derivatives  
Molecular Framework Aromatic homomonocyclic compounds
Substituents Dibenzylbutane lignan skeleton - Phenylpropane - Catechol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Benzenoid - Monocyclic benzene moiety - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound
Description This compound belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety.
External Descriptors a small molecule

Associated Targets(Human)

HSD17B2 Tchem Estradiol 17-beta-dehydrogenase 2 (1 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
SNCA Tchem Alpha-synuclein (2 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
TRPA1 Tclin Transient receptor potential cation channel subfamily A member 1 (1 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
ALOX12 Tchem Arachidonate 12-lipoxygenase, 12S-type (2 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
ALOX5 Tclin Arachidonate 5-lipoxygenase (10 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
ALOX15 Tchem Arachidonate 15-lipoxygenase (4 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
LTB4R Tchem Leukotriene B4 receptor 1 (1 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
CYP19A1 Tclin Aromatase (1 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
ABL1 Tclin Tyrosine-protein kinase ABL (18331 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ESR1 Tclin Estrogen receptor alpha (17718 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
AR Tclin Androgen Receptor (11781 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
VDR Tclin Vitamin D receptor (26531 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CYP19A1 Tclin Cytochrome P450 19A1 (6099 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MAOA Tclin Monoamine oxidase A (11911 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MAOB Tclin Monoamine oxidase B (8835 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
PTH1R Tclin Parathyroid hormone receptor (47172 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
IGF1R Tclin Insulin-like growth factor I receptor (8605 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CSNK1D Tchem Casein kinase I delta (4546 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
LTB4R Tchem Leukotriene B4 receptor 1 (1083 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ALOX15B Tchem Arachidonate 15-lipoxygenase, type II (7244 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ALOX12 Tchem Arachidonate 12-lipoxygenase (3262 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HSD17B1 Tchem Estradiol 17-beta-dehydrogenase 1 (2224 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
S1PR1 Tclin Sphingosine 1-phosphate receptor Edg-1 (5806 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
C5AR1 Tclin C5a anaphylatoxin chemotactic receptor (2677 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (36611 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HSD17B2 Tchem Estradiol 17-beta-dehydrogenase 2 (1671 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
AURKA Tchem Serine/threonine-protein kinase Aurora-A (10240 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
TP53 Tchem Cellular tumor antigen p53 (48468 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Homo sapiens (32628 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
A-375 (9258 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
A498 (42825 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ACHN (49357 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
BGC-823 (3035 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CAKI-1 (44928 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CCRF-CEM (65223 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
COLO 205 (50209 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
DU-145 (51482 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HL-60 (67320 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HT-29 (80576 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
K562 (73714 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
KM12 (47707 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
M14 (47487 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MCF7 (126967 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MOLT-4 (49676 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
OVCAR-3 (48710 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
OVCAR-4 (44535 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Associated Targets(non-human)

Ttr Transthyretin (14 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Aplnr Apelin receptor (201 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Mapk1 MAP kinase ERK2 (650 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Hdac6 Histone deacetylase 6 (222 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Fgfr3 Fibroblast growth factor receptor 3 (21 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Plasmodium yoelii yoelii (73 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Spinacia oleracea (250 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Human alphaherpesvirus 2 (4932 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Human respirovirus 3 (1674 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Mus musculus (284745 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Vaccinia virus (4609 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Human alphaherpesvirus 1 (11089 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Sindbis virus (1599 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Vesicular stomatitis virus (4460 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Influenza A virus (11224 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Punta Toro virus (1491 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Coxsackievirus B4 (2249 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Respiratory syncytial virus (3434 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
L929 (3802 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
LOX1.1 Seed lipoxygenase-1 (463 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
5-lipoxygenase (33 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Hsf1 Heat shock factor protein 1 (5445 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Luciferin 4-monooxygenase (66902 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
rep Replicase polyprotein 1ab (378 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Trpa1 Transient receptor potential cation channel subfamily A member 1 (1003 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Gpr119 Glucose-dependent insulinotropic receptor (270 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ddn Putative uncharacterized protein (49 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Feline coronavirus (624 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Mammalian orthoreovirus 1 (1523 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Large T antigen (1457 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Mapt Microtubule-associated protein tau (6 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
pos-1 Cytoplasmic zinc-finger protein (1690 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
mex-5 Zinc finger protein mex-5 (1676 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Lipoxygenase (149 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
GCGR Uncharacterized protein (2 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
G6PD-6PGL Glucose-6-phosphate dehydrogenase-6-phosphogluconolactonase (1761 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
clpP ATP-dependent Clp protease proteolytic subunit (245 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
rmlD dTDP-4-dehydrorhamnose reductase (49 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
LOX1.4 Seed linoleate 9S-lipoxygenase (11 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Vero C1008 (1716 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Mechanisms of Action

Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References

Names and Identifiers

IUPAC Name 4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
INCHI InChI=1S/C18H22O4/c1-11(7-13-3-5-15(19)17(21)9-13)12(2)8-14-4-6-16(20)18(22)10-14/h3-6,9-12,19-22H,7-8H2,1-2H3
InChIKey HCZKYJDFEPMADG-UHFFFAOYSA-N
Smiles CC(CC1=CC(=C(C=C1)O)O)C(C)CC2=CC(=C(C=C2)O)O
Isomeric SMILES CC(CC1=CC(=C(C=C1)O)O)C(C)CC2=CC(=C(C=C2)O)O
WGK Germany 3
RTECS UX1750000
Molecular Weight 302.37
Beilstein 6(1)577
Reaxy-Rn 9803564
Reaxys-RN_link_address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=9803564&ln=

Certificates（CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:

Chemical and Physical Properties

Melt Point(°C) 184-188℃
Molecular Weight 302.400 g/mol
XLogP3 4.300
Hydrogen Bond Donor Count 4
Hydrogen Bond Acceptor Count 4
Rotatable Bond Count 5
Exact Mass 302.152 Da
Monoisotopic Mass 302.152 Da
Topological Polar Surface Area 80.900 Ų
Heavy Atom Count 22
Formal Charge 0
Complexity 303.000
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 2
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
The total count of all stereochemical bonds 0
Covalently-Bonded Unit Count 1

Citations of This Product

How to Cite Aladdin Scientific Products?
1. Bin Wang, Xin-Li Xu, Man-Yu Zhang, Xin-Miao Bu, Hong-Lei Wang, Xue-Zhong Shi, Xia Xu, Di Chen.  (2023)  A fully green sample preparation method for synthetic antioxidants determination in edible oils based on natural feather fiber-supported liquid extraction.  JOURNAL OF CHROMATOGRAPHY A,  1698  (464004). 
2. Jinhua Zhu, Danyang Zhou, Dandan Wu, Wei Liu, Xiuhua Liu.  (2022)  TiO2 nanotube immobilised 5-lipoxygenase-mediated screening and isolation of anti-inflammatory active compounds from the leaves of lonicera japonica thunb.  JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY,  37  (1): (2540-2550). 
3. Yuling Li, Xiaotong Wu, Zixuan Wu, Mingmin Zhong, Xiaoping Su, Youai Ye, Yan Liu, Lei Tan, Yong Liang.  (2022)  Colorimetric sensor array based on CoOOH nanoflakes for rapid discrimination of antioxidants in food.  Analytical Methods,  14  (28): (2754-2760). 
4. Han Xueyuan, Wang Xiaoyu, Shen Chi, Mo Yiwei, Tian Rungang, Mao Linchun, Luo Zisheng, Yang Huanyi.  (2022)  Exogenous ABA promotes aroma biosynthesis of postharvest kiwifruit after low-temperature storage.  PLANTA,  255  (4): (1-13). 
5. Xue Cheng, Guan Si-Cong, Chen Jian-Qing, Wen Chen-Jin, Cai Jian-Fa, Chen Xu.  (2020)  Genome wide identification and functional characterization of strawberry pectin methylesterases related to fruit softening.  BMC PLANT BIOLOGY,  20  (1): (1-17). 
6. Shi Yuru, Zhang Xiaoqian, Pei Shengji, Wang Yuhua.  (2024)  Ethnopharmacological study on Adenosma buchneroides Bonati inhibiting inflammation via the regulation of TLR4/MyD88/NF-κB signaling pathway.  Natural Products and Bioprospecting,  14  (1): (1-12). 

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