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Nordihydroguaiaretic acid

Product Name
Nordihydroguaiaretic acid
CAS No.
500-38-9
Chemical Name
Nordihydroguaiaretic acid
Synonyms
NDGA;ACTINEX;NSC 4291;TIMTEC-BB SBB005930;LABOTEST-BB LT00233087;NDGA, LARREA DIVARICATA;nordihydroguaiareticaci;dihydronorguaiareticacid;dihydro-norguaiareticaci;NORDIHYDROGUAIRETIC ACID
CBNumber
CB5755745
Molecular Formula
C18H22O4
Formula Weight
302.36
MOL File
500-38-9.mol
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Nordihydroguaiaretic acid Property

Melting point:
184-186 °C (lit.)
Boiling point:
363.4°C (rough estimate)
Density 
1.0772 (rough estimate)
refractive index 
1.4230 (estimate)
storage temp. 
Inert atmosphere,Room Temperature
solubility 
DMSO (Slightly), Methanol (Slightly)
pka
9.56±0.10(Predicted)
form 
Powder
color 
White to off-white
Water Solubility 
slightly soluble
Merck 
14,6693
BRN 
2056825
Stability:
Stable. Incompatible with oxidizing agents.
LogP
4.640 (est)
CAS DataBase Reference
500-38-9(CAS DataBase Reference)
NIST Chemistry Reference
Pyrocatechol, 4,4'-(2,3-dimethyltetramethylene)di-(500-38-9)
EPA Substance Registry System
Nordihydroguaiaretic acid (500-38-9)
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Safety

Hazard Codes 
Xn
Risk Statements 
22-36/37/38
Safety Statements 
26-36/37-37/39-24/25-22
WGK Germany 
3
RTECS 
UX1750000
HS Code 
29072990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
74540
Product name
Nordihydroguaiaretic acid
Purity
≥97.0% (HPLC)
Packaging
1g
Price
$98.3
Updated
2024/03/01
Sigma-Aldrich
Product number
479975
Product name
NDGA
Packaging
250mg
Price
$85.2
Updated
2024/03/01
TCI Chemical
Product number
D0800
Product name
Nordihydroguaiaretic Acid
Purity
>97.0%(HPLC)
Packaging
1g
Price
$111
Updated
2024/03/01
TCI Chemical
Product number
D0800
Product name
Nordihydroguaiaretic Acid
Purity
>97.0%(HPLC)
Packaging
5g
Price
$363
Updated
2024/03/01
Alfa Aesar
Product number
L03149
Product name
Nordihydroguaiaretic acid, 97%
Packaging
1g
Price
$80.4
Updated
2024/03/01
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Nordihydroguaiaretic acid Chemical Properties,Usage,Production

Description

Nordihydroguaiaretic acid (NDGA) is a grayish-white crystalline compound that was widely used as an antioxidant in animal fats in the 1950s and 1960s. It possesses phenolic properties similar to gallates, including their advantages and disadvantages. Besides the isolation of natural material (resinous exudate of creosote bush), NDGA has also been chemically synthesized. As the result of unfavorable toxicological findings, NDGA is prohibited from use in the US. More specifically, NDGA is a potent lipoxygenase inhibitor which interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carbox- ylesterase,and,to a lesser extent, cyclooxygenase.

Chemical Properties

Nordihydroguaiaretic acid is a white to light yellow crystalline powder. Melting range 183～185℃. Insoluble in water. Slightly soluble in hot water. Soluble in alcohol, ether, glycerol, propylene glycol. About 0.5% is dissolved in oil. It has good antioxidant effect and is also effective against mildew. It has a synergistic effect when used in combination with citric acid and ascorbic acid.

Uses

Nordihydroguaiaretic acid is used in the treatment of multiple diseases, including cardiovascular diseases, neurological disorders and cancers. It is also used as an antioxidant.

Definition

ChEBI: 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.

Preparation

Nordihydroguaiaretic acid is obtained by hydrodemethylation of dimethyl ether of guaiacolinic acid, a component of guaiac resin. It is also produced from desert plant, creosote bush (Larrea divaricata Cav. Or Corillea tridentate), which can be widely found in the border zone of southern of USA and northern of Mexico.

Application

Nordihydroguaiaretic acid (NDGA, 500-38-9) is an antioxidant that has poor solubility and shows evidence of discoloration in the presence of metal salts. It is used to a limited extent to retard rancidity. NDGA is a broad bean lipoxygenase inhibitor that polyphenol-bearing o-dihydroxy (catechol) structure. The oxidation product from Resveratrol (R150000) showed a high inhibitory activity, w hereas Resveratrol itself had no activity and its oxidation efficiency was low.

benefits

Nordihydroguaiaretic acid is a kind of antioxidant compound presented in the creosoten bush. It is a potent in vitro scavenger of many kind of oxidants such as peroxynitrite, singlet oxygen, hydroxyl radical, superoxide anion and hypochlorous acid. Studies have shown that it has various physiological effects. It can also protect hippocampal neurons against amyloid β-peptide toxicity, and attenuates free radical and calcium accumulation. Rat study has shown that it can block the synaptic component of long-term potentiation and the associated increases in release of glutamate and arachidonate. Two most exciting results are that: (1) it has the potential to increase lifespan of animals; (2) it can suppress growth of breast cancer cells through inhibiting the IGF-1 and c-erbB2/HER/NEU receptors.

General Description

Nordihydroguaiaretic acid (NDGA) is used as an powerful antioxidant and potent scavenger of reactive oxygen species (ROS). NDGA is a phenolic lignan obtained from Larrea tridentata, that has been used in traditional medicine for the treatment of numerous diseases such as cancer, renal, cardiovascular, immunological, and neurological disorders, and even aging.

Hazard

Use in foods prohibited by FDA.

Biochem/physiol Actions

Lipoxygenase inhibitor; polyphenol-bearing o-dihydroxy (catechol) structure.

Safety Profile

Moderately toxic by intraperitoneal route. An antioxidant food additive. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Crystallise the acid from dilute acetic acid. [Beilstein 6 IV 7771.]

References

Floriano-Sánchez, E, et al. "Nordihydroguaiaretic acid is a potent in vitro scavenger of peroxynitrite, singlet oxygen, hydroxyl radical, superoxide anion and hypochlorous acid and prevents in vivo ozone-induced tyrosine nitration in lungs." Free Radical Research 40.5(2006):523.
Goodman, Yadong, et al. "Nordihydroguaiaretic acid protects hippocampal neurons against amyloid β-peptide toxicity, and attenuates free radical and calcium accumulation." Brain Research 654.1(1994):171.
Lynch, M. A., M. L. Errington, and T. V. Bliss. "Nordihydroguaiaretic acid blocks the synaptic component of long-term potentiation and the associated increases in release of glutamate and arachidonate: an in vivo study in the dentate gyrus of the rat." Neuroscience 30.3(1989):693-701.
Strong, Randy, et al. "Nordihydroguaiaretic acid and aspirin increase lifespan of genetically heterogeneous male mice." Aging Cell 7.5(2008):641-650.
Youngren, Jack F., et al. "Nordihydroguaiaretic Acid (NDGA) Inhibits the IGF-1 and c-erbB2/HER2/neu Receptors and Suppresses Growth in Breast Cancer Cells." Breast Cancer Research & Treatment 94.1(2005):37-46.

Nordihydroguaiaretic acid Preparation Products And Raw materials

Raw materials

GUM GUAIAC

Preparation Products

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View Lastest Price from Nordihydroguaiaretic acid manufacturers

Shaanxi Dideu New Materials Co. Ltd
Product
Nordihydroguaiaretic acid 500-38-9
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
97.0%
Supply Ability
10000KGS
Release date
2024-11-19
Hebei Yanxi Chemical Co., Ltd.
Product
Nordihydroguaiaretic acid 500-38-9
Price
US $40.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
10 tons
Release date
2023-09-21
Hebei Mojin Biotechnology Co., Ltd
Product
Nordihydroguaiaretic acid 500-38-9
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2024-10-22

500-38-9, Nordihydroguaiaretic acidRelated Search:

Citric acid Hydroxytyrosol Acetate Apigenin Resveratrol Ethanol Guaifenesin Potassium Bitartrate Potassium guaiacolsulfonate hemihydrate GUM GUAIAC Folic acid Ethyl 2-(Chlorosulfonyl)acetate Guaiacol Hyaluronic acid Ascoric Acid Masoprocol 2,3-Dimethylbutane Nordihydroguaiaretic acid

  • 4,4’-(2,3-dimethyltetramethylene)di-pyrocatecho
  • beta,gamma-Dimethyl-alpha,delta-bis(3,4-dihydroxyphenyl)butane
  • Butane, 1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethyl-
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  • [-CH(CH3)CH2C6H3-1,2-(OH)2]2
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  • NSC 4291
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  • Nordihydroguaiaretic acid - pure diastereomer
  • Nordihydroguairaretic acid
  • nordihydroguairareticacid
  • Norguaiaretic acid, dihydro-
  • Pyrocatechol, 4,4'- (2,3-diemthyltetramethylene) di-
  • ACTINEX
  • 1,4-BIS(3,4-DIHYDROXYPHENYL)-2,3-DIMETHYLBUTANE
  • 1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-
  • 1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethyl-butan
  • 2,3-Bis(3,4-dihydroxyphenylmethyl)butane
  • 4,4'-(2,3-Dimethyl-1,4-Butanediyl)bis(pyrocatechol)
  • NORDIHYDROGUAIARETIC ACID
  • NORDIHYDROGUAIRETIC ACID
  • NDGA
  • NDGA, LARREA DIVARICATA
  • TIMTEC-BB SBB005930
  • NORDIHYDROGUAIARETIC ACID TAN CRYSTALS INHIBITOR OF LIPOXYGENASES
  • 4,4'-(2,3-DIMETHYLTETRAMETHYLENE)DIPYROCATECHOL (NORDIHYDROGUAIARETIC ACID)
  • Nordihydroguaiareticacid,97%
  • LABOTEST-BB LT00233087
  • 4,4'-(2,3-DIMETHYL-1,4-BUTANEDIYL)BIS-1,2-BENZENEDIOL
  • 4,4'-(2,3-DIMETHYLTETRAMETHYLENE)DIPYROCATECHOL
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  • 500-38-9
  • HO2C6H3CH2CHCH32
  • -CHCH3CH2C6H312OH22