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500-38-9

Basic Information
CAS No.: 500-38-9
Name: Nordihydroguaiaretic acid
Article Data: 5
Molecular Structure:
Molecular Structure of 500-38-9 (Nordihydroguaiaretic acid)
Formula: C18H22O4
Molecular Weight: 302.37
Synonyms: Pyrocatechol,4,4'-(2,3-dimethyltetramethylene)di- (8CI);1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane;4,4'-(2,3-Dimethyl-1,4-butanediyl)bis(pyrocatechol);4-[4-(3,4-Dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol;Butane,1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethyl-;Dihydronorguaiaretic acid;Dinorguaiaretic acid, dihydro-;NDGA;NSC 4291;Norguaiaretic acid, dihydro-;b,g-Dimethyl-a,d-bis(3,4-dihydroxyphenyl)butane;
EINECS: 207-903-0
Density: 1.241 g/cm3
Melting Point: 182-187 °C
Boiling Point: 526.5 °C at 760 mmHg
Flash Point: 247.8 °C
Solubility: slightly soluble in water
Appearance: light yellow crystalline solid
Hazard Symbols: HarmfulXn
Risk Codes: 22-36/37/38
Safety: 26-36/37/39-24/25-22
PSA: 80.92000
LogP: 3.56640
Synthetic route
5701-82-6

1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane

500-38-9

nordihydroguaiaretic acid

Conditions
ConditionsYield
With hydrogen bromide In water at 126℃; for 10h; Reagent/catalyst; Inert atmosphere;91.26%
meso-2.3-bis-<3.4-carbonyldioxy-benzyl>-butane

meso-2.3-bis-<3.4-carbonyldioxy-benzyl>-butane

500-38-9

nordihydroguaiaretic acid

Conditions
ConditionsYield
With hydrogenchloride
63-91-2

L-phenylalanine

A

7400-08-0

para-coumaric acid

B

500-38-9

nordihydroguaiaretic acid

Conditions
ConditionsYield
With Larrea divaricata Cav. callus cells In ethanol Enzymatic reaction;
776-99-8

3,4-dimethoxyphenylacetone

500-38-9

nordihydroguaiaretic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: titanium tetrachloride; zinc / tetrahydrofuran / 5 h / Inert atmosphere; Reflux
1.2: 2 h / 20 °C / Inert atmosphere
2.1: trifluoroacetic acid; HSiPh3 / dichloromethane / 48.5 h / 20 °C / Inert atmosphere
3.1: hydrogen bromide / water / 10 h / 126 °C / Inert atmosphere
View Scheme
102-09-0

bis(phenyl) carbonate

500-38-9

nordihydroguaiaretic acid

5,5'-(2,3-dimethylbutane-1,4-diyl)bis(benzo[d][1,3]dioxol-2-one)

Conditions
ConditionsYield
With triethylamine In diethyl ether at 20℃; for 48h;90.8%
3674-13-3

2,3-dibromopropionic acid ethyl ester

500-38-9

nordihydroguaiaretic acid

C28H34O8

Conditions
ConditionsYield
With potassium carbonate In acetone for 18h; Reflux;85.5%
75-09-2

dichloromethane

500-38-9

nordihydroguaiaretic acid

77150-81-3

5,5'-(2,3-dimethylbutane-1,4-diyl)bis(benzo[d][1,3]dioxole)

Conditions
ConditionsYield
With sodium hydroxide In dimethyl sulfoxide at 120℃;73%
78-39-7

Triethyl orthoacetate

500-38-9

nordihydroguaiaretic acid

5,5'-(2,3-dimethylbutane-1,4-diyl)bis(2-ethoxy-2-methylbenzo[d][1,3]dioxole)

Conditions
ConditionsYield
With Amberlyst-15 In toluene at 100℃;69.2%
52-90-4

L-Cysteine

500-38-9

nordihydroguaiaretic acid

5′-S-cysteinylnordihydroguaiaretic acid

Conditions
ConditionsYield
With peroxidase from horseradish; dihydrogen peroxide In methanol; water at 25℃; Enzymatic reaction;20%
500-38-9

nordihydroguaiaretic acid

5701-82-6

1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane

Conditions
ConditionsYield
In diethyl ether for 5h;2.4%
Raw Materials
63-91-2
Downstream Products
120-80-9
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Specification

The 1,2-Benzenediol,4,4'-(2,3-dimethyl-1,4-butanediyl)bis-, with the CAS registry number 500-38-9, is also known as 2,3-Dimethyl-1,4-bis(3,4-dihydroxyphenyl)butane. It belongs to the product category of Aromatic Phenols. Its EINECS number is 207-903-0. This chemical's molecular formula is C18H22O4 and molecular weight is 302.36. What's more, its systematic name is 4,4'-(2,3-dimethylbutane-1,4-diyl)dibenzene-1,2-diol. Its classification codes are: (1)Analgesics; (2)Analgesics, Non-Narcotic; (3)Anti-Inflammatory Agents; (4)Anti-Inflammatory Agents, Non-Steroidal; (5)Antioxidants; (6)Cyclooxygenase inhibitors; (7)Enzyme Inhibitors; (8)Lipoxygenase inhibitors; (9)Mutation data; (10)Peripheral Nervous System Agents; (11)Protective Agents; (12)Sensory System Agents. It should be sealed and stored in a cool, ventilated and dry place. Moreover, it should be protected from oxides. It is a potent antioxidant compound found in the long-lived creosote bush. It serves as an antioxidant in fats and oils. It is stable but incompatible with strong oxidizing agents.

Physical properties of 1,2-Benzenediol,4,4'-(2,3-dimethyl-1,4-butanediyl)bis- are: (1)ACD/LogP: 3.71; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.71; (4)ACD/LogD (pH 7.4): 3.71; (5)ACD/BCF (pH 5.5): 390.1; (6)ACD/BCF (pH 7.4): 385.63; (7)ACD/KOC (pH 5.5): 2490.88; (8)ACD/KOC (pH 7.4): 2462.34; (9)#H bond acceptors: 4; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 36.92 Å2; (13)Index of Refraction: 1.626; (14)Molar Refractivity: 86.26 cm3; (15)Molar Volume: 243.4 cm3; (16)Polarizability: 34.19×10-24cm3; (17)Surface Tension: 57.3 dyne/cm; (18)Density: 1.241 g/cm3; (19)Flash Point: 247.8 °C; (20)Enthalpy of Vaporization: 83.1 kJ/mol; (21)Boiling Point: 526.5 °C at 760 mmHg; (22)Vapour Pressure: 1.06E-11 mmHg at 25°C.

Preparation: this chemical can be prepared by the hydrogenation of guaiac-based fatty acid dimethyl ether, and then getting rid of the methyl.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed. It is irritating to eyes, respiratory system and skin. You should not breathe dust. When using it, you must avoid contact with skin and eyes. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)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
(2)InChIKey: HCZKYJDFEPMADG-UHFFFAOYSA-N
(3)Canonical SMILES: CC(CC1=CC(=C(C=C1)O)O)C(C)CC2=CC(=C(C=C2)O)O

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 830mg/kg (830mg/kg)   Advances in Food Research. Vol. 3, Pg. 197, 1951.
mouse LD50 intraperitoneal 550mg/kg (550mg/kg)   Advances in Food Research. Vol. 3, Pg. 197, 1951.
mouse LD50 oral 2gm/kg (2000mg/kg)   Journal of the American Oil Chemists' Society. Vol. 54, Pg. 239, 1977.
rat LD50 oral 2gm/kg (2000mg/kg)   Journal of the American Oil Chemists' Society. Vol. 54, Pg. 239, 1977.