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, being present in the blood 5 minutes after oral administration, and reaching its peak plasma concentration in about 10 minutes. Its elimination from the blood is usually as rapid.
Excreted by rabbits in combined form with sulfate (15%) and glucuronic acid (72%).
CREOSOTE IS RAPIDLY ABSORBED FROM THE GASTROENTERIC TRACT AND THROUGH THE SKIN. IT APPEARS TO BE EXCRETED IN THE URINE MAINLY IN CONJUGATION WITH SULFURIC, HEXURONIC, & OTHER ACIDS. OXIDATION ALSO OCCURS WITH THE FORMATION OF CMPD THAT IMPART A SMOKY APPEARANCE TO THE URINE. TRACES ARE EXCRETED BY WAY OF THE LUNGS.
Medical experience indicates that toxic quantities can be absorbed through the skin quite readily.
Methoxyphenol largely absorbed from digestive tract and stored in blood, kidneys, and respiratory organs. Excreted by rabbits in combined form with sulfate (15%) and glucuronic acid (72%).
In rats, guaiacol is rapidly absorbed, being present in the blood 5 minutes after oral administration, and reaching its peak plasma concentration in about 10 minutes. Its elimination from the blood is usually as rapid.

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Metabolism / Metabolites
.../IT APPEARS TO BE CONJUGATED/ WITH SULFURIC, HEXURONIC & OTHER ACIDS. OXIDATION...OCCURS WITH FORMATION OF COMPOUNDS THAT IMPART A SMOKY APPEARANCE TO THE URINE.
Several strains of Aspergillus niger hydroxylated anisole to give o-hydroxyanisole as main product.
o-Methoxyphenol yields 3-methoxycatechol probably in rabbit; yields o-methoxyphenyl sulfate probably in rabbit. o-Methoxyphenol yields catechol in rat; yields 1,2-dimethoxybenzene in mouse, rabbit, guinea pig, and rat. /From table/

Toxicity Data
LC50 (mice) = 7,570 mg/m3

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Interactions
Methoxyphenol has been found to contribute to the carcinogenic effect of tobacco smoke in rats.
Absorption was delayed when ibuprofen and guaiacol administered simultaneously.

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Non-Human Toxicity Values
LD50 Mouse male oral 525 mg/kg
LD50 Rat female oral 870 mg/kg
LD50 Rat male oral 885 mg/kg
LD50 Mouse subcutaneous 6.25-12.5 ug
LD50 Rat oral 725 mg/kg
LD50 Mouse oral 621 mg/kg
LD50 Rat 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 appears as colorless to amber crystals or liquid. Density (of solid) 1.129 g / cm3. Solidifies at 28 °C (82.4 °F), but may remain liquid for a long time even at a much lower temperature. Slightly water soluble. Soluble in aqueous sodium hydroxide. Used medicinally as an expectorant. Used, because of its anti-oxidant properties, as an anti-skinning agent for paints.
Guaiacol is a monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position. It has a role as an expectorant, a disinfectant, a plant metabolite and an EC 1.1.1.25 (shikimate dehydrogenase) inhibitor. It is functionally related to a catechol.
Guaiacol is an agent thought to have disinfectant properties and used as an expectorant. Guaiacol is a phenolic natural product first isolated from Guaiac resin and the oxidation of lignin. Guaiacol is also present in wood smoke, as a product of pyrolysis of lignin. Guaiacol has been found in the urine of patients with neuroblastoma and pheochromocytoma.
Guaiacol has been reported in Angelica gigas, Rhodotorula mucilaginosa, and other organisms with data available.
Guaiacol is a phenolic compound with a methoxy group and is the monomethyl ether of catechol. Guaiacol is readily oxidized by the heme iron of peroxidases including the peroxidase of cyclooxygenase (COX) enzymes. It therefore serves as a reducing co-substrate for COX reactions. Guaiacol is a phenolic natural product first isolated from Guaiac resin and the oxidation of lignin. It is a yellowish aromatic oil that is now commonly derived from guaiacum or wood creosote. It is used medicinally as an expectorant, antiseptic, and local anesthetic. Guaiacol is used in traditional dental pulp sedation, and has the property of inducing cell proliferation; guaiacol is a potent scavenger of reactive oxygen radicals and its radical scavenging activity may be associated with its effect on cell proliferation. Guaiacol is also used in the preparation of synthetic vanillin. Guaiacol is also present in wood smoke, as a product of pyrolysis of lignin. Guaiacol has been found in the urine of patients with neuroblastoma and pheochromocytoma. (A3556, A3559).
2-methoxyphenol is a metabolite found in or produced by Saccharomyces cerevisiae.
An agent thought to have disinfectant properties and used as an expectorant. (From Martindale, The Extra Pharmacopoeia, 30th ed, p747)
See also: Wood Creosote (part of); Tolu balsam (USP) (part of); Creosote (annotation moved to).

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Drug Indication
It is used medicinally as an expectorant, antiseptic, and local anesthetic. Guaiacol is used in traditional dental pulp sedation, and has the property of inducing cell proliferation; guaiacol is a potent scavenger of reactive oxygen radicals and its radical scavenging activity may be associated with its effect on cell proliferation.

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Therapeutic Uses
IT IS USED EMPIRICALLY AS AN EXPECTORANT TO LESSEN AMT OF MUCOUS IN THE CHRONIC STAGES OF BRONCHITIS & BRONCHIECTASIS. IT IS FREQUENTLY PRESCRIBED FOR ITS STIMULANT EXPECTORANT ACTION AS A CONSTITUENT OF A STEAM INHALANT. THE ANTISEPTIC ACTION IS WEAK & NOT CLINICALLY USEFUL. ... IT HAS BEEN EMPLOYED AS A LOCAL ANESTHETIC IN DENTISTRY, IN A MANNER SIMILAR TO THYMOL. IT IS OCCASIONALLY EMPLOYED EXTERNALLY FOR ITS DISINFECTANT ACTION.
MEDICATION (VET): TOPICALLY (1.0-1.5%), IN UDDER AND WOUND TREATMENT OINTMENTS & IN POULTICES; WHEN ELIMINATED BY RESP MUCOUS MEMBRANES, SLIGHT ANTISEPTIC & LOCAL ANESTHETIC EFFECTS MAY OCCUR. INTERNALLY ... USED IN ANTIFERMENT & ANTIBLOAT MIXTURES.
ANTIPYRETIC; STYPTIC; ASTRINGENT
MEDICATION (VET): PARASITICIDE, DEODORANT
Disinfectants; Expectorants
Medication (Vet): ... Oral or parenteral mucolytic antiseptic antitussive in bronchopneumonias. ... Inhalant. In antiphlogistic, anodyne liquids on congested udders, in horse leg paints, and in poultices. Spray over tail biting swine to ... discourage cannibalism. Parenteral /dosage/ in camphorated oil. US mfr use 50 mg/mL concentration.
For the symptomatic relief of coughs associated with colds, bronchial catarrh, influenza and upper respiratory tract infections such as laryngitis and pharyngitis. Codeine is a well-known centrally acting cough suppressant. Guaiacol acts as an expectorant, loosening bronchial secretions in the respiratory tract. /Guaiacol, codeine combination/

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Drug Warnings
THE REPEATED ABSORPTION OF THERAPEUTIC DOSES FROM GASTROENTERIC TRACT MAY INDUCE SIGNS OF CHRONIC INTOXICATION, CHARACTERIZED BY DISTURBANCES OF VISION & DIGESTION (INCR PERISTALSIS & EXCRETION OF BODY FECES). IN ISOLATED CASES OF "SELF-MEDICATION", HYPERTENSION & ALSO GENERAL CARDIOVASCULAR COLLAPSE HAVE BEEN DESCRIBED.
WHEREVER CREOSOTE IS INDICATED FOR INTERNAL MEDICATION CREOSOTE FROM WOOD TAR SHOULD BE DISPENSED & UNDER NO CIRCUMSTANCES SHOULD CREOSOTE FROM COAL TAR BE GIVEN, UNLESS EXPLICITLY SO DIRECTED.
Do not 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.)