Nordihydroguaiaretic acid

ChemicalBook > CAS DataBase List > Nordihydroguaiaretic acid

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

Less

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)
form: Powder
pka: 9.56±0.10(Predicted)
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)

Less

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

Less

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.

Less

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

Less

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

Less

Nordihydroguaiaretic acid Suppliers

Americas 1 Belgium 1 Canada 1 China 185 Denmark 1 Europe 1 France 1 Germany 4 India 9 Japan 4 Switzerland 4 United Kingdom 11 United States 50 Global 273

Shanghai Boyle Chemical Co., Ltd.

Tel: 021-50182298 021-50180596
Fax: +86-21-57758967
Email: sales@boylechem.com
Country: China
ProdList: 2210
Advantage: 55

J & K SCIENTIFIC LTD.

Tel: 010-82848833 400-666-7788
Fax: 86-10-82849933
Email: jkinfo@jkchemical.com
Country: China
ProdList: 96815
Advantage: 76

Meryer (Shanghai) Chemical Technology Co., Ltd.

Tel: 021-61259108 18621169109
Fax: 86-21-61259102
Email: market03@meryer.com
Country: China
ProdList: 40240
Advantage: 62

Alfa Aesar

Tel: 400-6106006
Fax: 021-67582001/03/05
Email: saleschina@alfa-asia.com
Country: China
ProdList: 30132
Advantage: 84

TCI (Shanghai) Development Co., Ltd.

Tel: 021-67121386
Fax: 021-67121385
Email: Sales-CN@TCIchemicals.com
Country: China
ProdList: 24539
Advantage: 81

Energy Chemical

Tel: 021-021-58432009 400-005-6266
Fax: 021-58436166
Email: sales8178@energy-chemical.com
Country: China
ProdList: 44700
Advantage: 61

Chemsky（shanghai）International Co.,Ltd.

Tel: 021-50135380
Email: shchemsky@sina.com
Country: China
ProdList: 32344
Advantage: 50

Shandong Xiya Chemical Co., Ltd

Tel: 13355009207 13355009207
Fax: 0539-6365991
Email: 3007715519@qq.com
Country: China
ProdList: 18739
Advantage: 57

Syntechem Co.,Ltd

Tel
Fax: E-Mail Inquiry
Email: info@syntechem.com
Country: China
ProdList: 12990
Advantage: 57

China Langchem Inc.

Tel: 0086-21-58956006
Fax: 0086-21-58956100
Country: China
ProdList: 7815
Advantage: 57

Aemon Chemical

Tel: 0086-755-86198205
Email: acinfo@aemonchem.com
Country: China
ProdList: 1937
Advantage: 57

Dalian Meilun Biotech Co., Ltd.

Tel: 0411-62910999 13889544652
Email: sales@meilune.com
Country: China
ProdList: 4664
Advantage: 58

ShangHai YuanYe Biotechnology Co., Ltd.

Tel: 021-61312847 13636370518
Fax: 021-55068248
Email: shyysw007@163.com
Country: China
ProdList: 4941
Advantage: 60

Thermo Fisher Scientific

Tel: 800-810-5118
Fax: +86-10-84193589
Email: cnchemical@thermofisher.com
Country: China
ProdList: 17779
Advantage: 75

Beijing innoChem Science & Technology Co.,Ltd.

Tel: 400-810-7969 010-59572699
Fax: 010-59572688
Email: ningzi.li@inno-chem.com.cn
Country: China
ProdList: 6139
Advantage: 55

Haoyuan Chemexpress Co., Ltd.

Tel: 021-58950125
Fax: (86) 21-58955996
Email: info@chemexpress.com
Country: China
ProdList: 7553
Advantage: 61

9ding chemical ( Shanghai) Limited

Tel: 4009209199
Fax: 86-021-52271987
Email: sales@9dingchem.com
Country: China
ProdList: 22519
Advantage: 55

Shanghai Aladdin Bio-Chem Technology Co.,LTD

Tel: 18521735133 18521732826;
Fax: 021-50323701
Email: market@aladdin-e.com
Country: China
ProdList: 25014
Advantage: 65

Shanghai Tauto Biotech Co., Ltd.

Tel: 021-51320588
Fax: 0086-21-51320502
Email: tauto@tautobiotech.com
Country: China
ProdList: 3989
Advantage: 66

Guangzhou Isun Pharmaceutical Co., Ltd

Tel: 020-39119399 18927568969
Fax: 020-39119999
Email: isunpharm@qq.com
Country: China
ProdList: 4428
Advantage: 55

TargetMol Chemicals Inc.

Tel: 021-021-33632979 15002134094
Fax: 021-33632979
Email: marketing@targetmol.com
Country: China
ProdList: 7854
Advantage: 58

Bide Pharmatech Ltd.

Tel: 400-1647117 15221909166
Fax: +86-21-61629029
Email: product02@bidepharm.com
Country: China
ProdList: 41438
Advantage: 60

Shanghai Aspire Biological Technology Co., Ltd.

Tel: 021-61317773
Fax: 021-61486878
Email: sales@aspirebio.com
Country: China
ProdList: 2881
Advantage: 58

Shanghai Macklin Biochemical Co.,Ltd.

Tel: 15221275939 15221275939
Fax: 021-50706099
Email: shenlinxing@macklin.cn
Country: China
ProdList: 15878
Advantage: 55

Hangzhou J&H Chemical Co., Ltd.

Tel: +86-571-87396432
Fax: 0571-87396431
Email: sales@jhechem.com
Country: China
ProdList: 10015
Advantage: 53

Shanghai Yongye Biotechnology Co., Ltd.

Tel: 86-021-61559134 15921386130
Fax: 021-55068248
Email: 3423497944@qq.com
Country: China
ProdList: 8147
Advantage: 55

Hubei Jusheng Technology Co.,Ltd

Tel: 027-59599241 18871490274
Fax: 027-59599241
Email: 1400878000@qq.com
Country: China
ProdList: 9972
Advantage: 58

Chizhou Kailong Import and Export Trade Co., Ltd.

Tel
Fax: -
Email: xg01_gj@163.com
Country: China
ProdList: 9503
Advantage: 50

Sigma-Aldrich

Tel: 021-61415566 800-8193336
Email: orderCN@merckgroup.com
Country: China
ProdList: 51471
Advantage: 80

Alta Scientific Co., Ltd.

Tel: 022-6537-8550 15522853686
Fax: 022-2532-9655
Email: sales@altasci.com.cn
Country: China
ProdList: 4515
Advantage: 55

Wuhan ChemFaces Biochemical Co., Ltd.

Tel: 18607101326 15172504745
Fax: +86-27-84254680
Email: aileen@chemfaces.com
Country: China
ProdList: 7059
Advantage: 55

Henan CoreyChem Co., Ltd

Tel: 0371-86658258
Fax: 0371-60996044
Email: info@coreychem.com
Country: China
ProdList: 10457
Advantage: 58

Shanghai EFE Biological Technology Co., Ltd.

Tel: 021-65675885 18964387627
Fax: 021-65675885
Email: info@efebio.com
Country: China
ProdList: 9709
Advantage: 58

Guangzhou QiYun Biotechnology Co., Ltd.

Tel: 020-61288194 61288195
Fax: 020-61288700
Email: 505721671@qq.com
Country: China
ProdList: 3868
Advantage: 58

Chengdu Dianchun Technology Co., Ltd

Tel: 400-1166-196 18502815961
Fax: QQ：800101999
Email: cdhxsj@163.com
Country: China
ProdList: 14623
Advantage: 60

Shanghai ChengShao Biological Technology Co., Ltd.

Tel: 021-61847300 13341622919
Fax: 021-61847300
Email: shcss01@163.com
Country: China
ProdList: 4809
Advantage: 58

Beijing Solarbio Science & Tecnology Co., Ltd.

Tel: 010-50973130 4009686088
Email: 3193328036@qq.com
Country: China
ProdList: 29796
Advantage: 68

Beijing Jin Ming Biotechnology Co., Ltd.

Tel: 010-60605840 18892239720
Fax: 010-60605840
Email: psaitong@jm-bio.com
Country: China
ProdList: 12308
Advantage: 58

Shanghai Yihe Biological Technology Co., Ltd.

Tel: 17721395025
Fax: 021-68882955
Email: 2423903095@qq.com
Country: China
ProdList: 3154
Advantage: 58

Shenzhen Sendi Biological Technology Co., Ltd.

Tel: 18124570582 TEL：0755-23574479 2355327139
Fax: 0755-23229476 QQ: 2355327139
Email: siliao02@yccreate.com
Country: China
ProdList: 6120
Advantage: 58

Taian Jiaye Biotechnology Co.Ltd

Tel: 13127280945
Email: 285424065@qq.com
Country: China
ProdList: 9980
Advantage: 55

Guangzhou Jhd Chemical Reagent Co., Ltd.

Tel: 020-84383047
Fax: 020-84380294
Email: sales@jhd.com.cn
Country: China
ProdList: 9190
Advantage: 65

9ding chemical ( Shanghai) Limited

Tel: 021-021-52271985 17721149837
Fax: +86 (21) 52271987
Email: sales@9dingchem.com
Country: China
ProdList: 19806
Advantage: 60

Wuhan Netcom Electronic Commerce Limited

Tel: 18064670521
Fax: 0757-88210752
Email: 2355935187@ycphar.com
Country: China
ProdList: 4887
Advantage: 58

Guangzhou LES biological Technology Co.,Ltd.

Tel: 13672434928
Fax: -
Email: 3307355104@qq.com
Country: China
ProdList: 3650
Advantage: 58

Zhuhai JiaYi Biological Technology Co., Ltd.

Tel: 18578209868 2355327026
Fax: 18578209868 QQ：2355327026
Email: steroidbest@hotmail.com
Country: China
ProdList: 6504
Advantage: 58

Aikon International Limited

Tel: 025-58851090 13611564524
Fax: (6)02557626880
Email: lwan@aikonchem.com
Country: China
ProdList: 15952
Advantage: 58

Linyi Azelasi Biological Co., Ltd.

Tel: 17753923223
Fax: 0539-6222546
Email: 2805221329@qq.com
Country: China
ProdList: 1474
Advantage: 58

Hefei Yaogu Biological Technology Co., Ltd.

Tel: 0086-0551-62993905
Fax: 0086-0551-62993905
Email: info@hxygmall.com
Country: China
ProdList: 3374
Advantage: 58

Tianjin heowns Biochemical Technology Co., Ltd.

Tel: 400-6387771-6038 18902104717
Email: sales@heowns.com
Country: China
ProdList: 20532
Advantage: 60

Less

View Lastest Price from Nordihydroguaiaretic acid manufacturers

Henan Fengda Chemical Co., Ltd

Product: Nordihydroguaiaretic acid 500-38-9
Price: US $10.00-2.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: g-kg-tons, free sample is available
Release date: 2024-04-28

Hebei Yanxi Chemical Co., Ltd.

Product: Nordihydroguaiaretic acid 500-38-9
Price: US $40.00-40.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 10 tons
Release date: 2023-09-21

Meike meditech (Foshan) Co.,Ltd

Product: Nordihydroguaiaretic acid 500-38-9
Price: US $0.00-0.00/g
Min. Order: 100g
Purity: 97%
Supply Ability: 100kg
Release date: 2023-09-18

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-

dihydro-dinorguaiareticaci

Dihydronorguaiaretic acid

dihydro-norguaiareticaci

dihydronorguaiareticacid

Dinorguaiaretic acid, dihydro-

1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane, 4,4μ-(2,3-Dimethyltetramethylene)dipyrocatechol, Masoprocol, NDGA

4,4'-(2,3-Dimethyl-1,4-butylene)dipyrocatechol

4,4'-(2,3-Dimethylbutane-1,4-diyl)bis(benzene-1,2-diol)

Nordihydroguaiaretic acid,95%

[-CH(CH3)CH2C6H3-1,2-(OH)2]2

Nordihydroguaiaretic acid,1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane, 4,4′-(2,3-Dimethyltetramethylene)dipyrocatechol, Masoprocol, NDGA

Nordihydroguaiaretic acid, tech. 90%

To a dihydro-nordihydroguaiaretic acid

Nordihydroguaiaretic acid, 95% 500MG

Nordihydro Guaiaretic Acid (Mixture of diastereoMers)

NSC 4291

β,γ-DiMethyl-α,δ-bis(3,4-dihydroxyphenyl)butane

NDGA 4,4'-(2,3-Dimethyltetramethylene)dipyrocatechol

Nordihydroguaiaretic acid >=97.0% (HPLC)

NDGA (Nordihydroguaiaretic acid)

2,6-Di-tert-butyl-4-methylphenol Solution, 1000ppm

NDGA - CAS 500-38-9 - Calbiochem

1,4-Bis(3,4-Dihydroxyphenyl)-2,3-Dimethylbutanenordihydroguaiaretic Acid

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

Nordihydroguaiaretic Acid &gt

Nordihydroguaiaretic Acid Standard

Nordihydroguaiaretic acid USP/EP/BP

nordihydroguaiareticaci

4,4'-(2,3-Dimethylbutane-1,4-diyl)bis(benzene-1,2-diol)

500-38-9

HO2C6H3CH2CHCH32

-CHCH3CH2C6H312OH22

Oxygen Compounds

Polyols