CAS 500-38-9|CAS 845-69-2|4,4'-[2,3-Dimethyl-1,4-butanediyl]-bis[1,2-benzenediol|nordihydroguaiaretic acid|NORDIHYDROGUAIARETIC ACID|4-{3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl}benzene-1,2-diol|...

General Information

Structure

Molecular Formula

C₁₈H₂₂O₄

Molecular Mass

302.36488

Exact Mass

302.15180918

Charge

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

Canonic Smiles

CC(C(Cc1ccc(c(c1)O)O)C)Cc1ccc(c(c1)O)O

Isomeric Smiles

CC(Cc1cc(O)c(O)cc1)C(C)Cc1cc(O)c(O)cc1

Calculated Properties

JChem

LogD (pH = 7.4)

4.75

LogD (pH = 5.5)

4.76

Log P

4.76

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

9.21

Polar Surface Area

80.92

Polarizability

33.55

Molar Refractivity

86.62

LOG S

-4.16

Data Source

Names and Identifiers

Synonyms

4,4'-[2,3-Dimethyl-1,4-butanediyl]-bis[1,2-benzenediolNORDIHYDROGUAIARETIC ACID去甲二氢愈创木酸NDGANordihydroguaiaretic acid马索罗酚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Masoprocol1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane4,4′-(2,3-Dimethyltetramethylene)dipyrocatecholNordihydroguaiaretic AcidNordihydroguaiaretateDihydronorcodeineDihydronorguaiaretic AcidNor DihydrocodeineNordihydro Guaiaretic Acid (mixture of diastereomers)β,γ-Dimethyl-α,δ-bis(3,4-dihydroxyphenyl)butane(5α,6α)-4,5-Epoxy-3-methoxymorphinan-6-ol4,4'-(2,3-Dimethyltetramethyl-ene)dipyrocatechol4,5α-Epoxy-3-methoxy-morphinan-6α-ol4,4'-(2,3-Dimethyl-1,4-butanediyl)bis-1,2-benzenediolNSC 4291Nordihydrocodeinenorhydroguaiaretic acidbeta,gamma-dimethyl-alpha,delta-bis(3,4-dihydroxyphenyl)butane2,3-bis(3,4-dihydroxyphenylmethyl)butanenordihydroguaiaretic acidNSC 42911,4-bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane4,4'-(2,3-dimethyl-1,4-butanediyl)bis(pyrocatechol)nordihydroguaiaretic acid (unspecified)NDGAnordihydroguaiaretic acid4,4'-(2,3-dimethyltetramethylene)dipyrocatechol

IUPAC Traditional name

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

IUPAC name

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

Names and Identifiers

Registration numbers

Properties

Safety Information

Harmful (Xn)

Pharmacology Properties

human ... ALOX15(246), PTGS1(5742), PTGS2(5743)mouse ... Alox12(11684)

mouse ... Alox12(11684)

human ... ALOX15(246), PTGS1(5742), PTGS2(5743)

Leukotriene antagonist

Antioxidant

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02155944

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

05212974

MP Biomedicals Rare Chemical collection

Wikipedia

Nordihydroguaiaretic_acid

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。

N2036

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

N1144

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

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

TRC

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

N672700

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

ChEBI

CHEBI:7625

A tetrol that is butane which is substituted at positions 2 and 3 by 3,4-dihydroxybenzyl groups. Masoprocol, the meso-form found in the leaves of the creosote bush (Larrea divaricata), is a potent lipoxygenase inhibitor.

Molecule Details

References

PubChem Literature

From Data Sources

• Ammon, S., et al.: Brit. J. Clin. Pharmacol., 48, 317 (1985)

• Bartlett, S., et al.: Life Sci., 57, 609 (1985)

• Schwanstecher, M., et al.: J. Neurochem., 59, 1325 (1985)

• Lahti, R., et al.: Eur. J. Pharmacol., 109, 281 (1985)

• Ridolfi, M., et al.: J. Agric. Food Chem., 50, 835 (1999)

• Brash, A., et al.: J. Biol. Chem., 274, 23679 (1999)

• Fujimoto, A., et al.: Bioorg. Med. Chem. Lett., 20, 7393 (1999)

• Naturally-occurring antioxidant.

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

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

IUPAC name

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

Molecule Details

MP Biomedicals

02155944

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

05212974

MP Biomedicals Rare Chemical collection

Wikipedia

Nordihydroguaiaretic_acid

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。

N2036

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

N1144

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

74540

TRC

N673000

N672700

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

ChEBI

CHEBI:7625

References

PubChem Literature

From Data Sources

• Ammon, S., et al.: Brit. J. Clin. Pharmacol., 48, 317 (1985)

• Bartlett, S., et al.: Life Sci., 57, 609 (1985)

• Schwanstecher, M., et al.: J. Neurochem., 59, 1325 (1985)

• Lahti, R., et al.: Eur. J. Pharmacol., 109, 281 (1985)

• Ridolfi, M., et al.: J. Agric. Food Chem., 50, 835 (1999)

• Brash, A., et al.: J. Biol. Chem., 274, 23679 (1999)

• Fujimoto, A., et al.: Bioorg. Med. Chem. Lett., 20, 7393 (1999)

• Naturally-occurring antioxidant.

Bioactivity

PubChem BioAssay

Properties

Safety Information

Harmful (Xn)

Pharmacology Properties

human ... ALOX15(246), PTGS1(5742), PTGS2(5743)mouse ... Alox12(11684)

mouse ... Alox12(11684)

human ... ALOX15(246), PTGS1(5742), PTGS2(5743)

Leukotriene antagonist

Antioxidant

Molecule

ID:104439