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Nordihydroguaiaretic acid

Nordihydroguaiaretic acid structure

CAS No:
500-38-9
Formula:
C18H22O4
Chemical Name:
Nordihydroguaiaretic acid
Synonyms:
1,2-Benzenediol,4,4′-(2,3-dimethyl-1,4-butanediyl)bis-;Pyrocatechol,4,4′-(2,3-dimethyltetramethylene)di-;4,4′-(2,3-Dimethyl-1,4-butanediyl)bis[1,2-benzenediol];Butane,1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethyl-;Dihydronorguaiaretic acid;β,γ-Dimethyl-α,δ-bis(3,4-dihydroxyphenyl)butane;4,4′-(2,3-Dimethyltetramethylene)dipyrocatechol;Dinorguaiaretic acid,dihydro-;NDGA;Nordihydroguaiaretic acid;Norguaiaretic acid,dihydro-;4,4′-(2,3-Dimethyl-1,4-butanediyl)bis(pyrocatechol);1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane;NSC 4291;4-[4-(3,4-Dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol;1413-68-9
Categories:
Cosmetic Ingredient > Antioxidant Ingredient

Description

Nordihydroguaiaretic acid is a 5-lipoxygenase (5LOX) (IC50=8±3 μM) and tyrosine kinase inhibitor.

Nordihydroguaiaretic acid is 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. It has a role as an antioxidant, a plant metabolite, a ferroptosis inhibitor and a geroprotector. It is a member of catechols, a tetrol and a lignan.|A potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent. It also serves as an antioxidant in fats and oils.

Nordihydroguaiaretic acid Basic Attributes

Molecular Weight：

302.36

Exact Mass：

302.36

BRN：

2056825

EC Number：

207-903-0

NSC Number：

682984|4291

DSSTox ID：

DTXSID5022437

HScode：

2907299090

Characteristics

PSA：

80.9

XLogP3：

4.3

Appearance：

White to off-white Powder

Density：

1.2±0.1 g/cm3

Melting Point：

185.5 °C

Boiling Point：

526.5ºC at 760 mmHg

Flash Point：

247.8±23.3 °C

Refractive Index：

1.627

Water Solubility：

H2O: slightly soluble

Storage Conditions：

Freezer (-20°C)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

22-36/37/38

safety instructions：

26-36/37-37/39-24/25-22

RTECS Number：

UX1750000

Marks：

Stability/Shelf Life：

Stable. Incompatible with oxidizing agents.

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H302-H315-H319-H335

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 262 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes. (See all compounds classified as Cyclooxygenase Inhibitors.)|Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)|Compounds that bind to and inhibit that enzymatic activity of LIPOXYGENASES. Included under this category are inhibitors that are specific for lipoxygenase subtypes and act to reduce the production of LEUKOTRIENES. (See all compounds classified as Lipoxygenase Inhibitors.)

MeSH Entry Terms：

(R*,S*)-4,4'-(2,3-Dimethylbutane-1,4-diyl)bispyrocatechol

Nordihydroguaiaretic acid Use and Manufacturing

Methods of Manufacturing

It is derived from the guaiac acid dimethyl ether hydrodemethylation of guaiac resin. It can also be obtained by extracting beech leaves with alkaline solution, crystallizing under acidic conditions, and decomposing by adding water.

Uses

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 oxidation efficiency was low.

Manufacturing Info：

1,2-Benzenediol, 4,4'-[(2R,3S)-2,3-dimethyl-1,4-butanediyl]bis-, rel-: INACTIVE

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Food Additives -> ANTIOXIDANT; -> JECFA Functional Classes|Cosmetics -> Antioxidant

Food Additive Classes：

Food Additives -> ANTIOXIDANT;

Computed Properties

Molecular Weight:302.4
XLogP3:4.3
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:302.15180918
Monoisotopic Mass:302.15180918
Topological Polar Surface Area:80.9
Heavy Atom Count:22
Complexity:303
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Guide of Nordihydroguaiaretic acid

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties
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