Basic information
- Standard SMILES
CC(Cc1ccc(O)c(O)c1)C(C)Cc1ccc(O)c(O)c1- InChIKey
HCZKYJDFEPMADG-UHFFFAOYSA-N- Molecular formula
- C18H22O4
- Average molar mass
- 302.4 g/mol
- Monoisotopic mass
- 302.15180918
Overview
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 a ferroptosis inhibitor, a geroprotector, an antioxidant and a plant metabolite. It is a lignan, a member of catechols and a tetrol.
Names & identifiers
- Preferred name
- Nordihydroguaretic acid
- IUPAC
- 4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
- English name
- Nordihydroguaiaretic acid
- Molecular formula
- C18H22O4
- Molecular weight
- 302.36
Names & synonyms
nordihydroguaretic acid2,3-bis(3,4-dihydroxybenzyl)butaneRefChem:854717NORDIHYDROGUAIARETIC ACID500-38-9NDGA4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diolNorhydroguaiaretic acidNorguaiaretic acid, dihydro-1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-NSC 42914,4'-(2,3-Dimethyltetramethylene)dipyrocatechol
Show more names
ACTINEXNORDIHYDROGUAIRETIC ACIDTIMTEC-BB SBB005930LABOTEST-BB LT00233087NDGA, LARREA DIVARICATAnordihydroguaiareticacidihydronorguaiareticaciddihydro-norguaiareticaci
MFCD000022062,3-Bis(3,4-dihydroxyphenylmethyl)butaneDTXSID5022437Pyrocatechol, 4,4'-(2,3-dimethyltetramethylene)di-4,4'-(2,3-Dimethyl-1,4-butanediyl)bis(pyrocatechol)nordihydroguaiaretateCHEMBL52Butane, 1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethyl-
Database identifiers
- CAS
500-38-9- PubChem CID
- 4534
- DTXSID
DTXSID5022437- ChEMBL
CHEMBL52- ChEBI
CHEBI:7625- EC Number
- 207-903-0
- Nikkaji
- J9.195B
Properties
Computed structural properties
- XLogP
- 4.3
- Topological polar surface area
- 80.9 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 303
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Plant Toxins
CosmeticsAntioxidant
Food AdditivesANTIOXIDANT -> FDA Substance added to food
Endocrine DisruptorsPotential endocrine disrupting compound
Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical DescriptionSolid; [Merck Index] White odorless powder; [Alfa Aesar MSDS]
Collision Cross Section167.5 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID5022437]
Physicochemical properties
- Melting point
- 184 · 184-186 °C (lit.)
- Boiling point
- 363.4 °C · 363.4°C (rough estimate)
- Density
- 1.0772 · 1.0772 (rough estimate)
- refractive index
- 1.423 · 1.4230 (estimate)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Powder
- pka
- 9.56 · 9.56±0.10(Predicted)
- color
- White to off-white
- biological source
- Larrea divaricata (creosote bush)
- Water Solubility
- slightly soluble
- Merck
- 14 · 14,6693
- BRN
- 2056825 · 2056825
- Stability
- Stable. Incompatible with oxidizing agents.
- Cosmetics Ingredients Functions
- ANTIOXIDANT
- 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
- SMILES
- CC(Cc1ccc(O)c(O)c1)C(C)Cc2ccc(O)c(O)c2
- LogP
- 4.64 · 4.640 (est)
- Substances Added to Food (formerly EAFUS)
- NORDIHYDROGUAIARETIC ACID--PROHIBITED WITH EXCEPTIONS
- FDA 21 CFR
- 175.3 · 175.300; 177.1010; 181.24
- CAS DataBase Reference
- 500 · 500-38-9(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- NCI Dictionary of Cancer Terms
- Actinex; NDGA; nordihydroguaiaretic acid
- FDA UNII
- 7 PZ73W4ZNR · 7PZ73W4ZNR
- NCI Drug Dictionary
- Actinex
- NIST Chemistry Reference
- 4 · Pyrocatechol, 4,4'-(2,3-dimethyltetramethylene)di-(500-38-9)
- EPA Substance Registry System
- Nordihydroguaiaretic acid (500-38-9)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22-36/37/38
- Safety Statements
- 26 · 26-36/37-37/39-24/25-22
- WGK Germany
- 3 · 3
- RTECS
- 1750000 · UX1750000
- HS Code
- 29072990 · 29072990
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 188 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationChemical: 1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-
Hazards SummaryThis CAS# refers to the unspecified stereoisomer form; The meso- form is CAS# 27686-84-6; [Merck Index] A skin and strong eye irritant; Harmful by ingestion; [Alfa Aesar MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- UX1750000
- hs_code
- 29072990
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 26-36/37-37/39-24/25-22
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
Uses
Occurs in the creosote bush; Used as an antioxidant in foods and as an antineoplastic; [Merck Index]
Banned for use as an antioxidant in food; [EPA]
Use Classification
Food Additives -> ANTIOXIDANT -> JECFA Functional Classes
Food Additives -> ANTIOXIDANT -> JECFA Functional Classes
Cosmetics -> Antioxidant
Applications
DescriptionNordihydroguaiaretic 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.
UsesNordihydroguaiaretic acid is used in the treatment of multiple diseases, including cardiovascular diseases, neurological disorders and cancers. It is also used as an antioxidant.
General DescriptionNordihydroguaiaretic 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.
Preparation methods
PreparationNordihydroguaiaretic 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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
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Additional notes
DefinitionChEBI: 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.
Related reactions
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