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Nordihydroguaiaretic acid

Catalog Number

ACM500389-2

CAS

500-38-9

Structure

IUPAC Name

4-[4-(3,4-Dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol

Synonyms

1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethyl-butan

Molecular Weight

302.36

Molecular Formula

C18H22O4

Canonical SMILES

CC(CC1=CC(=C(C=C1)O)O)C(C)CC2=CC(=C(C=C2)O)O

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

InChI Key

HCZKYJDFEPMADG-UHFFFAOYSA-N

Boiling Point

363.4 °C

Melting Point

184-186 °C(lit.)

Flash Point

247.8°C

Purity

95%

Density

1.0772 g/cm³

Solubility

water, 4.969 mg/L @ 25 °C (est)

Appearance

White to off-white powder

Storage

Inert atmosphere, room temperature

Active Content

95%

Physical State

Solid

Typical Applications

Use as antioxidant.
Use as enzymes inhibitor.

MSDS

Download MSDS

COA

Download COA

Spec Sheet

Download Spec Sheet

Case Study

Synthesis of Tetra-O-Acetyl Nordihydroguaiaretic Acid Derivative from Nordihydroguaiaretic Acid (NDGA)

Synthesis of Tetra-O-Acetyl Nordihydroguaiaretic Acid Derivative from Nordihydroguaiaretic Acid (NDGA) John, Geraldine Sandana Mala, et al. Journal of Nanobiotechnology 18 (2020): 1-16.

Nordihydroguaiaretic acid (NDGA), a plant lignan derived from the creosote bush, is known for its antioxidant, anticancer, and antiviral properties and has been used in traditional medicine. Despite its medicinal benefits, toxicity studies have shown potential liver and kidney damage. Consequently, there has been growing interest in the chemical synthesis of NDGA derivatives for therapeutic applications. These derivatives offer promising alternatives to NDGA, including improved delivery to targeted tissues. In this context, an acetylated NDGA derivative, tetra-O-acetyl NDGA (Ac-NDGA), has been synthesized following a modified procedure.
Procedure:
Nordihydroguaiaretic acid (NDGA) (1.5 g, 4.96 mmol) was placed in a 100 mL screw-capped Erlenmeyer flask, and 3.0 mL (six times the molar amount of NDGA) of acetic anhydride was added in 1 mL aliquots, gently mixing after each addition. To the reaction mixture, 2.5 µL of concentrated sulfuric acid (H₂SO₄) was added, and the solution was shaken by hand until completely dissolved. The mixture was allowed to react overnight at room temperature to ensure full reaction completion.
Next, 10 mL of ice was added to another 100 mL Erlenmeyer flask, and the reaction mixture was poured in. A buttery yellow solid precipitated, which was filtered through a Buchner funnel under vacuum, washed with distilled water, and pressed to remove excess water. The pressed filter cake was then dissolved in 95% ethanol by heating to 80°C and allowed to cool at room temperature overnight for recrystallization.
The resulting tetra-O-acetyl NDGA crystals were collected by filtration in a Buchner funnel and dried in a vacuum desiccator overnight until they reached a constant weight. The filtrate was reserved for further recrystallization, and the same procedure was followed to isolate and weigh additional crystals.

Nordihydroguaiaretic Acid Prevents Glycation-Induced Structural Alterations and Aggregation of Albumin

Nordihydroguaiaretic Acid Prevents Glycation-Induced Structural Alterations and Aggregation of Albumin Awasthi, S., et al. International journal of biological macromolecules 122 (2019): 479-484.

This study investigates the antiglycation properties of Nordihydroguaiaretic acid (NDGA), a lignan extracted from the creosote bush (Larrea tridentata), which has been shown to offer therapeutic benefits for cancer, neurological disorders, and cardiovascular diseases.
We evaluated the antiglycation activity of NDGA using spectroscopic analysis, molecular interaction studies, and circular dichroism (CD) to assess its effects on albumin. Additionally, NDGA was found to inhibit the aggregation of albumin induced by glycation, as demonstrated by Thioflavin T binding assays and confocal imaging. The results indicate that NDGA is an effective inhibitor of advanced glycation end products (AGEs) formation. Furthermore, NDGA provided protective effects on albumin by preventing glycation-induced modification of key lysine residues (Lys20, Phe36, Lys41, Lys131, and Lys132).

Custom Q&A

What is the PubChem CID of Nordihydroguaiaretic acid?

PubChem CID 4534

What is the molecular formula of Nordihydroguaiaretic acid?

The molecular formula is C18H22O4.

What is the molecular weight of Nordihydroguaiaretic acid?

The molecular weight is 302.4 g/mol.

What is the IUPAC name of Nordihydroguaiaretic acid?

The IUPAC name is 4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol.

What are the synonyms for Nordihydroguaiaretic acid?

The synonyms include NORDIHYDROGUAIARETIC ACID, NDGA, Dihydronorguaiaretic acid, Actinex, and more.

What is the InChI of Nordihydroguaiaretic acid?

The InChI is 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.

What is the InChIKey of Nordihydroguaiaretic acid?

The InChIKey is HCZKYJDFEPMADG-UHFFFAOYSA-N.

What are the other identifiers for Nordihydroguaiaretic acid?

The other identifiers include CAS numbers (500-38-9, 27686-84-6, 1413-68-9), ChEMBL ID (CHEMBL52), DSSTox Substance ID (DTXSID5022437), KEGG ID (C10719), and more.

What is the XLogP3-AA value of Nordihydroguaiaretic acid?

The XLogP3-AA value is 4.3.

What is the hydrogen bond donor count of Nordihydroguaiaretic acid?

The hydrogen bond donor count is 4.

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