Guaiacol suppresses the expression of the COX-2 gene and the activation of NF-κB in response to lipopolysaccharide (LPS) in RAW 264.7 murine macrophage line cells. Phenolic substances, including phenol, eugenol, guaiacol, and vanillin, have a 50% inhibitory concentration on sheep vesicular gland prostaglandin cyclooxygenase. The sequence of reduction is as follows: phenol (1600 μM) > vanillin (>500 μM) > Guaiacol (72 μM) > Eugenol (12 μM) [1].

Absorption, Distribution and Excretion
In rats, guaiacol is rapidly absorbed, detectable in the blood within 5 minutes of oral administration, and reaches peak plasma concentrations in approximately 10 minutes. Its clearance from the blood is generally similarly rapid. In rabbits, guaiacol is primarily excreted as a conjugate of sulfate (15%) and glucuronic acid (72%). Creosote is rapidly absorbed from the gastrointestinal tract and skin. It appears to be primarily excreted in urine as a conjugate of sulfate, hexuronic acid, and other acids. Oxidation also generates CMPD, giving urine a smoky color. Trace amounts are excreted via the lungs. Medical experience suggests that toxic doses are readily absorbed through the skin. Methoxyphenol is primarily absorbed from the digestive tract and stored in the blood, kidneys, and respiratory organs. In rabbits, it is primarily excreted as a conjugate of sulfate (15%) and glucuronic acid (72%). In rats, guaiacol is rapidly absorbed, detectable in the blood within 5 minutes of oral administration, and reaches peak plasma concentrations within approximately 10 minutes. Its clearance from the blood is typically similarly rapid. Metabolites/Metabolites…/Appear to bind with sulfuric acid, hexuronic acid, and other acids. Oxidation reactions produce compounds that give urine a smoky color. Several Aspergillus niger strains can hydroxylate anisole, with o-hydroxyanisole as the major product. o-Methoxyphenol may generate 3-methoxycatechol in rabbits; o-methoxyphenyl sulfate may also be generated in rabbits. o-Methoxyphenol generates catechol in rats; and 1,2-dimethoxybenzene in mice, rabbits, guinea pigs, and rats. /Excerpt from a table/

Toxicity Data
LC50 (Mouse) = 7,570 mg/m³ Interactions Methoxyphenol has been found to exacerbate the carcinogenic effects of tobacco smoke in rats. Absorption is delayed when ibuprofen and guaiacol are administered concurrently. Non-human Toxicity Values LD50 Mice (Male) Oral: 525 mg/kg LD50 Rats (Female) Oral: 870 mg/kg LD50 Rats (Male) Oral: 885 mg/kg LD50 Mice (Subcutaneous): 6.25-12.5 μg LD50 Rats (Oral): 725 mg/kg LD50 Mice (Oral): 621 mg/kg LD50 Rats (Oral): 520 mg/kg

[1]. Re-evaluation of cyclooxygenase-2-inhibiting activity of vanillin and Guaiacol in macrophages stimulated with lipopolysaccharide. Anticancer Res. 2007 Mar-Apr;27(2):801-7.

o-Methoxyphenol is a colorless to amber crystal or liquid. Its solid density is 1.129 g/cm³. It solidifies at 28°C (82.4℉), but remains liquid for extended periods at temperatures far below this. It is slightly soluble in water and soluble in aqueous sodium hydroxide solution. It is used medically as an expectorant. Due to its antioxidant properties, it can be used as an anti-skinning agent in paints. Guaifenesin is a monomethoxybenzene formed by the ortho-substitution of phenol with a methoxy group. It possesses expectorant, antiseptic, phytometrogenic, and EC 1.1.1.25 (shikimate dehydrogenase) inhibitory effects. Its function is similar to that of catechol. Guaifenesin is considered to have antiseptic properties and is used as an expectorant. Guaifenesin is a natural phenolic product, initially isolated from guaiac resin and lignin oxidation. Guaifenesin is also present in wood smoke and is a product of lignin pyrolysis. Guaifenesin has also been found in the urine of patients with neuroblastoma and pheochromocytoma.
It has been reported that guaiacol is also found in Angelica sinensis, Rhodotorula glutinis, and other organisms with relevant data.
Guaicilol is a methoxylated phenolic compound and a monomethyl ether of catechol. Guaicilol is readily oxidized by heme iron in peroxidases, including cyclooxygenase (COX) peroxidase. Therefore, it can act as a reducing cosubstrate in COX reactions. Guaicilol is a natural phenolic product, initially isolated from guaiac resin and lignin oxidation. It is a pale yellow aromatic oil, now commonly extracted from guaiac wood or guaiacol oil. Medically, guaiacol is used as an expectorant, antiseptic, and local anesthetic. It is used in traditional pulp sedation and has cell proliferation-inducing properties; guaiacol is a potent scavenger of reactive oxygen species, and its free radical scavenging activity may be related to its cell proliferation-promoting effect. Guaicilol is also used in the synthesis of vanillin. Guaicilol is also present in wood smoke and is a product of lignin pyrolysis. Guaifenesin has also been found in the urine of patients with neuroblastoma and pheochromocytoma (A3556, A3559). 2-Methoxyphenol is a metabolite found or produced in Saccharomyces cerevisiae. It is considered to have antiseptic properties and is used as an expectorant. (From Martindale Pharmacopoeia, 30th edition, p. 747) See also: Guaifenesin oil (one of the ingredients); Toluene balsam (USP) (one of the ingredients); Creosote oil (note moved to). Medicinal Indications In medicine, it is used as an expectorant, antiseptic, and local anesthetic. Guaifenesin is used in traditional pulp sedation and has cell proliferation-inducing properties; it is a potent scavenger of reactive oxygen species, and its free radical scavenging activity may be related to its effect on cell proliferation. Therapeutic Uses In chronic bronchitis and bronchiectasis, it is empirically used as an expectorant to reduce mucus production. It is often used as an ingredient in steam inhalers to stimulate expectoration. Its antibacterial activity is weak, and its clinical application value is limited. ... It was once used as a local anesthetic in dentistry, similar to thymol. It is sometimes used externally for disinfection.
Drugs (Veterinary): External use (1.0-1.5%), used in ointments and creams for treating the breast and wounds; after being expelled through the respiratory mucosa, it may produce mild antibacterial and local anesthetic effects. Internal use... used in anti-fermentation and anti-flatulence mixtures.
Antipyretic; hemostatic; astringent.
Veterinary drugs: antiparasitic drugs, deodorants.
Disinfectants; expectorants.
Veterinary drugs: ...oral or injectable mucolytics, preservatives, antitussives, used to treat bronchopneumonia. ...Inhalants. Used as anti-inflammatory and analgesic solutions, applied to congested breasts, and in horse leg ointments and creams. Sprayed on pigs that bite their tails to...prevent cannibalism. Injection/Dosage/Dissolved in camphor oil. The concentration used by the US manufacturer is 50 mg/mL.
Used to relieve cough symptoms caused by colds, bronchial catarrh, influenza, and upper respiratory tract infections such as laryngitis and pharyngitis. Codeine is a well-known centrally acting antitussive. Guaifenesin is an expectorant that thins bronchial secretions in the respiratory tract. /Guaifenesin and codeine combination preparation/
Drug Warnings
Repeated absorption of therapeutic doses by the gastrointestinal tract may lead to chronic poisoning symptoms characterized by visual and digestive disturbances (increased intestinal motility and fecal excretion).
In isolated cases of "self-medication," hypertension and cardiovascular failure have been reported.
Where creosote is to be administered orally, creosote extracted from wood tar should be used; creosote extracted from coal tar should never be used unless explicitly instructed otherwise.
Not for use in cats.

C7H8O2

124.1372

124.052

90-05-1

Guaiacol-d3;74495-69-5;Guaiacol-d7;1065473-05-3;Guaiacol-13C6;202326-52-1;Guaiacol-d4;7329-52-4;Guaiacol-d4-1;20189-11-1

460

Colorless to light yellow <26°C powder,>29°C liquid

1.2±0.1 g/cm3

207.5±29.0 °C at 760 mmHg

26-29 °C(lit.)

79.3±24.3 °C

0.2±0.4 mmHg at 25°C

1.538

2.11

1

2

1

9

83

0

OC1C(OC)=CC=CC=1

LHGVFZTZFXWLCP-UHFFFAOYSA-N

InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3

2-methoxyphenol

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ≥ 100 mg/mL (~805.54 mM)
H2O : ~37.5 mg/mL (~302.08 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (20.14 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (20.14 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (20.14 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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Solubility in Formulation 4: 16.67 mg/mL (134.28 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

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 (Please use freshly prepared in vivo formulations for optimal results.)