4-{3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl}benzene-1,2-diol

• ChemBase ID: 104439
• Molecular Formular: C18H22O4
• Molecular Mass: 302.36488
• Monoisotopic Mass: 302.15180918
• SMILES: CC(Cc1cc(O)c(O)cc1)C(C)Cc1cc(O)c(O)cc1
• Canonical SMILES: CC(C(Cc1ccc(c(c1)O)O)C)Cc1ccc(c(c1)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
• InChIKey: HCZKYJDFEPMADG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl}benzene-1,2-diol
• IUPAC Traditional name: 4-{3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl}benzene-1,2-diol; nordihydroguaiaretic acid
• Synonyms: NDGA; Nordihydroguaiaretic acid; 1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane; 4,4′-(2,3-Dimethyltetramethylene)dipyrocatechol; Masoprocol; (5α,6α)-4,5-Epoxy-3-methoxymorphinan-6-ol; 4,5α-Epoxy-3-methoxy-morphinan-6α-ol; Dihydronorcodeine; Nordihydrocodeine; Nor Dihydrocodeine; 4,4'-(2,3-Dimethyl-1,4-butanediyl)bis-1,2-benzenediol; 4,4'-(2,3-Dimethyltetramethyl-ene)dipyrocatechol; Dihydronorguaiaretic Acid; NSC 4291; Nordihydroguaiaretic Acid; β,γ-Dimethyl-α,δ-bis(3,4-dihydroxyphenyl)butane; Nordihydro Guaiaretic Acid (mixture of diastereomers); Nordihydroguaiaretate; 4,4'-[2,3-Dimethyl-1,4-butanediyl]-bis[1,2-benzenediol; NORDIHYDROGUAIARETIC ACID; 1,4-双(3,4-二羟苯基)-2,3-二甲基丁烷; 4,4′-(2,3-二甲基四亚甲基)二邻苯二酚; 马索罗酚; 去甲二氢愈创木酸

Database IDs

• CAS Number: 500-38-9; 845-69-2
• EC Number: 207-903-0
• MDL Number: MFCD00002206
• Beilstein Number: 2056825; 2056826
• Merck Index: 146693
• PubChem SID: 24278590; 162091461; 24886494
• PubChem CID: 4534
• CHEMBL: 52
• MeSH Name: Nordihydroguaiaretic+acid
• Wikipedia Title: Nordihydroguaiaretic_acid

CALCULATED PROPERTIES

• Acid pKa: 9.206547
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 4.758438
• LogD (pH = 7.4): 4.7518115
• Log P: 4.7585225
• Molar Refractivity: 86.619 cm^3
• Polarizability: 33.23442 Å^3
• Polar Surface Area: 80.92 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Tan Solid
• Melting Point: 176-179°C (dec.); 184-186 °C(lit.); 184-186°C; 184-188°C

Safety Information

• Storage Condition: -20°C; Hygroscopic, Refrigerator, Under Inert Atmosphere
• RTECS: UX1750000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38; R:22
• Safety Statements: 26-36/37; S:36/37/39
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280H-P305+P351+P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... ALOX15(246), PTGS1(5742), PTGS2(5743); human ... ALOX15(246), PTGS1(5742), PTGS2(5743)mouse ... Alox12(11684); mouse ... Alox12(11684)
• Mechanism of Action: Antioxidant; Leukotriene antagonist

Product Information

• Purity: >97%; ≥90% (HPLC); ≥97.0% (HPLC); 97%
• Impurities: ≤2% water
• Biological Source: from Larrea divaricata (creosote bush); Isol. from Guaiacum officinale and Larrea sp.
• Application(s): Antioxidant
• Linear Formula: [-CH(CH3)CH2C6H3-1,2-(OH)2]2

DETAILS

MP Biomedicals - 02155944

(4,4'-[2,3-Dimethyl-1,4-butanediyl]-bis[1,2-benzenediol) White to Tan Crystalline Powder. Inhibitor of lipoxygenases

MP Biomedicals - 05212974

MP Biomedicals Rare Chemical collection

Sigma Aldrich - N5023

Biochem/physiol Actions
脂氧合酶抑制剂；含多酚的邻二羟基（儿茶酚）结构。

Sigma Aldrich - N1144

Biochem/physiol Actions
Lipoxygenase inhibitor; polyphenol-bearing o-dihydroxy (catechol) structure.

Sigma Aldrich - N2036

Biochem/physiol Actions
Lipoxygenase inhibitor; polyphenol-bearing o-dihydroxy (catechol) structure.
Other Notes
Synthetic

Sigma Aldrich - 74540

Application
antioxidant
Biochem/physiol Actions
Lipoxygenase inhibitor; polyphenol-bearing o-dihydroxy (catechol) structure.
Other Notes
Inhibitor of broad bean lipoxygenase1
Packaging
1, 5 g in glass bottle

Toronto Research Chemicals - N673000

Lipoxygenase inhibitor; polyphenol-bearing o-dihydroxy (catechol) structure. Inhibitor of broad bean lipoxygenase. The oxidation product from Resveratrol (R150000) showed a high inhibitory activity, whereas Resveratrol itself had no activity and its oxida

Toronto Research Chemicals - N672700

Nor Dihydrocodeine is a metabolite of Dihydrocodeine (D448850).This is a controlled substance.

REFERENCES

• Lahti, R., et al.: Eur. J. Pharmacol., 109, 281 (1985)
• Schwanstecher, M., et al.: J. Neurochem., 59, 1325 (1985)
• Bartlett, S., et al.: Life Sci., 57, 609 (1985)
• Ammon, S., et al.: Brit. J. Clin. Pharmacol., 48, 317 (1985)
• Brash, A., et al.: J. Biol. Chem., 274, 23679 (1999)
• Fujimoto, A., et al.: Bioorg. Med. Chem. Lett., 20, 7393 (1999)
• Ridolfi, M., et al.: J. Agric. Food Chem., 50, 835 (1999)
• Naturally-occurring antioxidant.