Guaiacol

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H8O2
Molecular Weight	124.1372
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(O)C=CC=C1

InChI

InChIKey=LHGVFZTZFXWLCP-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C7H8O2
Molecular Weight	124.1372
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.boots.com/wcsstore/cmsassets/Boots/Content/Products/Cough%20Cold%20Defence%20-%20CAT:%20A00000548/10068171.P/Pulmo%20Bailly%20PIL%5B1%5D.22133.1.pdf
Curator's Comment: Description was created based on several sources, including http://www.medicines.org.uk/emc/medicine/22147

Guaiacol is a naturally occurring organic compound first isolated by Otto Unverdorben in 1826. Although it is biosynthesized by a variety of organisms, this yellowish aromatic oil is usually derived from guaiacum or wood creosote. Guaiacol is used as a reducing co-substrate for COX reactions. It is mainly used as expectorant, antiseptic. It is used as cough suppressant, it is an ingredient of Pulmo Bailly (UK). Pulmo Bailly Cough Expectorant is indicated for relief for cough symptoms that are associated with a flu, cold, or other infection. It contains active ingredients, Codeine and Guajacol, which reduce discomfort and the urge to cough. Each 5 ml tablespoon of Pulmo Bailly contains 75 mg guaiacol and 7 mg codeine.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Free radical scavenging 5 Target ID: Free radical scavenging Sources: http://www.ncbi.nlm.nih.gov/pubmed/25582949	Activator 1447	0.03 µM [IC50]
intestine smooth muscle contraction 2 Target ID: GO:0014827 Sources: http://www.ncbi.nlm.nih.gov/pubmed/1455074	Inhibitor 8504	0.18 mM [IC50]
Carbonic anhydrase II 88 Target ID: CHEMBL205 Sources: http://www.ncbi.nlm.nih.gov/pubmed/19231207	Inhibitor 8504	2.94 µM [Ki]
Carbonic anhydrase I 62 Target ID: CHEMBL261 Sources: http://www.ncbi.nlm.nih.gov/pubmed/19231207	Inhibitor 8504	60.2 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cough 106 Sources: https://www.medicines.org.uk/emc/PIL.22133.latest.pdf?isAttachment=true&documentid=22133	Palliative		Approved 8583	Pulmo Bailly Approved Use Pulmo Bailly is indicated in adults for the symptomatic relief of coughs associated with colds, bronchial catarrh, influenza and upper respiratory tract infections such as laryngitis and pharyngitis.

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY41202	https://www.001chemical.com/chem/90-05-1
3B Scientific (Wuhan) Corp	3B1-00596	http://www.3bsc.com/index/pro_info.php?id=20808
3B Scientific (Wuhan) Corp	3B3-032623	http://www.3bsc.com/index/pro_info.php?id=53887
AA Blocks	AA003A7P	http://www.aablocks.com/goods/Goods/detail?id=AA003A7P
Aaron Chemicals	AR003AZH	http://www.aaronchem.com/90-05-1
abcr GmbH	AB117735	http://www.abcr.com/shop/en/AB117735
Aceschem	ACS014446	https://www.aceschem.com/catalog/90-05-1.html
Achemica	ACMC-209784	http://www.achemica.com/prodinfo/?id=118100
Achemtek	0104-001169	http://www.achemtek.com/90-05-1
Acorn PharmaTech	ACN-035755	http://www.acornpharmatech.com/
Acros Organics	AC120190010	https://www.fishersci.com/shop/products/guaiacol-99-acros-organics/AC120190010
Acros Organics	AC120190050	https://www.fishersci.com/shop/products/guaiacol-99-acros-organics-2/AC120190050
Acros Organics	AC120192500	https://www.fishersci.com/shop/products/guaiacol-99-acros-organics/AC120192500
AHH Chemical co.,ltd	MT-52200	http://www.ahhchemical.com/product/MT-52200.html
AHH Chemical co.,ltd	NP-1007	http://www.ahhchemical.com/product/NP-1007.html
AK Scientific, Inc. (AKSCI)	71383	http://www.aksci.com/item_detail.php?cat=71383
Alfa Aesar	A16319	https://www.alfa.com/en/catalog/A16319/
Alfa Chemistry	AP90051-A	https://reagents.alfa-chemistry.com/product/guaiacol-cas-90-05-1-18147.html
Alfa Chemistry	AP90051-B	https://reagents.alfa-chemistry.com/product/guaiacol-cas-90-05-1-18148.html
Alichem	490006743	http://www.alichem.com/en/products/90-05-1.html
Angene	AGN-PC-0WAJ1U	http://www.angenechemical.com/productshow/AGN-PC-0WAJ1U.html
Anward	ANW-13634	http://www.anward.com/pro_result/24333
Ark Pharm	AK114448	http://www.arkpharminc.com/products/90-05-1.html
Aurora Fine Chemicals LLC	A00.156.399	http://online.aurorafinechemicals.com/info?ID=A00.156.399
Aurora Fine Chemicals LLC	K02.105.305	http://online.aurorafinechemicals.com/info?ID=K02.105.305
Avantor Inc	200019-276	https://us.vwr.com/store/product/7514417/guaiacol
Avantor Inc	BT223270-1KG	https://us.vwr.com/store/product/16640262/guaiacol-98
Avantor Inc	BT223270-250G	https://us.vwr.com/store/product/16640262/guaiacol-98
Avantor Inc	BT223270-5KG	https://us.vwr.com/store/product/16640262/guaiacol-98
BioChemPartner	BCP27082	http://www.biochempartner.com/90-05-1-BCP27082
BioCrick	BCN8311	http://www.biocrick.com/Guaiacol-BCN8311.html
BioSynth	Q-100002	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-100002.html
BLD Pharm	BD35363	http://www.bldpharm.com/products/90-05-1.html
BOC Sciences	1065473-05-3	https://www.bocsci.com/2-methoxy-d3-phenol-3-4-5-6-d4-cas-1065473-05-3-item-155927.html
Chem Scene	CS-D1347	http://www.chemscene.com/90-05-1.html
ChemMol	49410542	http://www.chemmol.com/chemmol/49410542.html
ChemMol	99173681	http://www.chemmol.com/chemmol/99173681.html
Chemspace	CSSB00000210385	https://chem-space.com/CSSB00000210385
Clearsynth	CS-EB-01028	https://www.clearsynth.com/en/CSEB01028.html
Clearsynth	CS-ER-01020	https://www.clearsynth.com/en/CSER01020.html
Clearsynth	CS-T-91242	https://www.clearsynth.com/en/CST91242.html
CSNpharm	CSN16502	https://www.csnpharm.com/products/guaiacol.html
DC Chemicals	DCY-148	http://www.dcchemicals.com//product_show-Guaiacol.html
Debye Scientific	DB-024854	http://www.debyesci.com/DB-024854.html
Finetech	FT-0626815	http://www.finetechnology-ind.com/prod/detail/pub/90-05-1.html
Finetech	FT-0671312	http://www.finetechnology-ind.com/prod/detail/pub/74495-69-5.html
Glentham Life Sciences	GK7789	http://www.glentham.com/products/product/GK7789/
Hairui	HR128921	http://www.hairuichem.com/en/product/90-05-1.html
iChemical	EBD70419	http://www.ichemical.com/chemicals/cas-8021-39-4
Lab Network	LN00195361	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00195361
LGC Standards	DRE-C14056800	https://www.lgcstandards.com/US/en/p/DRE-C14056800
LGC Standards	LGCFOR0354.04	https://www.lgcstandards.com/US/en/p/LGCFOR0354.04
LGC Standards	MM0354.04	https://www.lgcstandards.com/US/en/p/MM0354.04
Matrix Scientific	206567	https://www.matrixscientific.com/206567.html
mcule	MCULE-5627336368	https://mcule.com/MCULE-5627336368/
MedChem Express	HY-N1380	https://www.medchemexpress.com/Guaiacol.html
Molcore	MC41202	https://www.molcore.com/product/90-05-1
MuseChem	R007592	https://www.musechem.com/product/R007592.html
MuseChem	R025087	https://www.musechem.com/product/R025087.html
Oakwood	241127	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=122126&ExtHyperLink=1
Otava	2826229	https://search.otavachemicals.com/#!/search?query=2826229&type=code&base=dbb
Parchem	13415	http://www.parchem.com/chemical-supplier-distributor/ortho-guaiacol-003415.aspx
Parchem	33140	http://www.parchem.com/chemical-supplier-distributor/Nat-Guaiacol-023140.aspx
Parchem	35467	http://www.parchem.com/chemical-supplier-distributor/Guaiacol-025467.aspx
Parchem	87167	https://www.parchem.com/chemical-supplier-distributor/Creosote--Beechwood-087167.aspx
R&D Chemicals	6208	http://www.rdchemicals.com/chemicals.php?mode=details&mol_id=7867
Sigma-Aldrich	12-1620_SAJ	https://www.sigmaaldrich.com/catalog/product/saj/121620?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1300004_USP	https://www.sigmaaldrich.com/catalog/product/usp/1300004?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	G5502_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/g5502?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	PHR1136_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/phr1136?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	V001359_VETEC	http://www.sigmaaldrich.com/catalog/product/vetec/v001359?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S575038	https://www.smolecule.com/products/s575038
TCI (Tokyo Chemical Industry)	M0121	http://www.tcichemicals.com/eshop/en/us/commodity/M0121/index.html
THE BioTek	bt-458615	https://www.thebiotek.com/product/others/bt-458615
VladaChem	VL143238	https://www.vladachem.com/product.php?products=90-05-1
VladaChem	VL163180	https://www.vladachem.com/product.php?products=90-05-1
VladaChem	VL250030	https://www.vladachem.com/product.php?products=90-05-1
VladaChem	VL269160-1KG	https://www.vladachem.com/product.php?products=90-05-1
Yuhao Chemical	LT7681	http://www.chemyuhao.com/1990-05-1.html

PubMed

Title	Date	PubMed
Polycyclic aromatic hydrocarbons disrupt axial development in sea urchin embryos through a beta-catenin dependent pathway.	2003-04-15	12604173
Amperometric biosensors based on recombinant laccases for phenols determination.	2003-03	12485779
Zonal changes in ascorbate and hydrogen peroxide contents, peroxidase, and ascorbate-related enzyme activities in onion roots.	2003-02	12586893
Effects of herbal drugs prescribed in wood creosote pills on the dissolution profile of guaiacol.	2003-02	12576679
Scaphopetalone and scaphopetalumate, a lignan and a triterpene ester from Scaphopetalum thonneri.	2003-02	12560041
Effect of culture conditions on manganese peroxidase production and activity by some white rot fungi.	2003-01	12545383
Effect of Mn2+, Co2+, Ni2+, and Cu2+ on horseradish peroxidase: activation, inhibition, and denaturation studies.	2003-01	12495207
Flavor composition of cashew (Anacardium occidentale) and marmeleiro (Croton species) honeys.	2002-12-18	12475279
Molecular cloning of a laccase isozyme gene from Pleurotus sajor-caju and expression in the heterologous Pichia pastoris host.	2002-12	12480904
Characterization of a low redox potential laccase from the basidiomycete C30.	2002-12	12473107
Examining reactivity and specificity of cytochrome c peroxidase by using combinatorial mutagenesis.	2002-11-04	12404635
Determination of 4-ethylguaiacol and 4-ethylphenol in red wines using headspace-solid-phase microextraction-gas chromatography.	2002-11-01	12456088
Psychobiologic responses to 4 days of increased training and recovery in cyclists.	2002-11	12439775
Purification and characterization of an extracellular laccase from the edible mushroom Lentinula edodes, and decolorization of chemically different dyes.	2002-11	12436315
Purification and characterization of soluble peroxidase from oil palm (Elaeis guineensis Jacq) leaf.	2002-11	12409016
Authentication of natural vanilla flavorings: isotopic characterization using degradation of vanillin into guaiacol.	2002-10-23	12381102
Mechanism-based irreversible inactivation of horseradish peroxidase at 500 MPa.	2002-10-05	12363360
Determination of phenols in landfill leachate-contaminated groundwaters by solid-phase extraction.	2002-10-04	12416875
Mesopone cytochrome c peroxidase: functional model of heme oxygenated oxidases.	2002-09-20	12237229
Replacement of active-site cysteine-436 by serine converts cytochrome P450 2B4 into an NADPH oxidase with negligible monooxygenase activity.	2002-09-20	12237221
Relationship of chemical structures of textile dyes on the pre-adaptation medium and the potentialities of their biodegradation by Phanerochaete chrysosporium.	2002-09-18	12234010
Alicyclobacillus acidiphilus sp. nov., a novel thermo-acidophilic, omega-alicyclic fatty acid-containing bacterium isolated from acidic beverages.	2002-09	12361274
Determination of minor and trace volatile compounds in wine by solid-phase extraction and gas chromatography with mass spectrometric detection.	2002-08-09	12214691
Changes of morphogenic competence in mature Pinus sylvestris L. buds in vitro.	2002-08	12197528
Purification, characterization, and chemical modification of manganese peroxidase from Bjerkandera adusta UAMH 8258.	2002-08	12070683
Effect of wash water temperature and chlorination on phenolic metabolism and browning of stored iceberg lettuce photosynthetic and vascular tissues.	2002-07-31	12137468
[Studies on production, purification and partial characteristics of the extracellular laccase from Armilliria mellea].	2002-07	12385243
Characterization of mefenamic acid-guaiacol ester: stability and transport across Caco-2 cell monolayers.	2002-07	12180533
Histological analysis of the maturation of native and wound periderm in potato (Solanum tuberosum L.) Tuber.	2002-07	12125762
Purification and characterisation of a novel laccase from the ascomycete Melanocarpus albomyces.	2002-07	12111146
Synthesis and antimicrotubule activity of combretatropone derivatives.	2002-06	11937347
Sensory and chemical changes in tomato sauces during storage.	2002-05-22	12009996
Comparison of temporal changes in components of formalin guaiacol under several storage conditions.	2002-05	12174665
[Decreased beta-phenylethylamine in urine of children with attention deficit hyperactivity disorder and autistic disorder].	2002-05	12030014
Isolation from a shea cake digester of a tannin-tolerant Escherichia coli strain decarboxylating p-hydroxybenzoic and vanillic acids.	2002-05	11927985
Sol-gel encapsulated horseradish peroxidase: a catalytic material for peroxidation.	2002-04-24	11960453
Analysis and expression of the class III peroxidase large gene family in Arabidopsis thaliana.	2002-04-17	12034502
Potent, orally active heterocycle-based combretastatin A-4 analogues: synthesis, structure-activity relationship, pharmacokinetics, and in vivo antitumor activity evaluation.	2002-04-11	11931625
Hydrogen peroxide protects tobacco from oxidative stress by inducing a set of antioxidant enzymes.	2002-04	12022476
Induction of apoptosis and caspase-3 activation by chemopreventive [6]-paradol and structurally related compounds in KB cells.	2002-03-08	11809529
Physiological activity of some aminophosphonates.	2002-02-12	11837690
Response of the cultivated tomato and its wild salt-tolerant relative Lycopersicon pennellii to salt-dependent oxidative stress: increased activities of antioxidant enzymes in root plastids.	2002-02	11999388
Involvement of peroxidases in the formation of the brown coloration of heartwood in Juglans nigra.	2002-02	11807134
Antioxidant enzymes and DPPH-radical scavenging activity in chilled and heat-shocked rice (Oryza sativa L.) seedlings radicles.	2002-01-30	11804522
Laccase production by some Phlebia species.	2002	12362400
Inhibition of mouse skin tumor promotion by anti-inflammatory diarylheptanoids derived from Alpinia oxyphylla Miquel (Zingiberaceae).	2002	12201673
Effects of yakuchinone A and yakuchinone B on the phorbol ester-induced expression of COX-2 and iNOS and activation of NF-kappaB in mouse skin.	2002	12086399
A note: gut bacteria produce components of a locust cohesion pheromone.	2002	11966918
[Effect of melatonin on release of beta-endorphin, norepinephrine and 5-hydroxytryptamine in rat brain].	2001-01	12579851
Detoxification of lignocellulose hydrolysates with ion-exchange resins.	2001	11963864

Patents

Sample Use Guides

In Vivo Use Guide

Adults: Up to two 5 ml teaspoonfuls should be taken in half a small glass of water three times daily before meals. A further two teaspoonfuls should be taken at bedtime to encourage undisturbed sleep. Sugar or fruit squash may be added if desired. Each 5 ml tablespoon of Pulmo Bailly contains 75 mg guaiacol and 7 mg codeine.

Route of Administration: Oral

In Vitro Use Guide

The 50% inhibition concentration required to decrease the cellular DNA contents by guaiacol was 9.8 mM in human dental pulp fibroblasts

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:55:08 GMT 2025` Edited by `admin` on `Mon Mar 31 17:55:08 GMT 2025`
Record UNII	6JKA7MAH9C
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

Guaiacol

Common Name

English

CREODON

Preferred Name

English

2-METHOXYPHENOL

Systematic Name

English

NSC-3815

Code

English

GUAIACOL [HSDB]

Common Name

English

GUAIACOL [MART.]

Common Name

English

GUAIACOL [USP-RS]

Common Name

English

2-METHOXYL-4-VINYLPHENOL

Systematic Name

English

GUAIACOL [MI]

Common Name

English

GUAIFENESIN IMPURITY A [EP IMPURITY]

Common Name

English

1-HYDROXY-2-METHOXYBENZENE

Systematic Name

English

GUAIACOL [JAN]

Common Name

English

GUAIACOL [FHFI]

Common Name

English

GUAIACOL [VANDF]

Common Name

English

Guaiacol [WHO-DD]

Common Name

English

(MU)-METHOXYPHENOL

Common Name

English

GUAIACOL [EP MONOGRAPH]

Common Name

English

GUAIACOL [USP IMPURITY]

Common Name

English

O-GUAIACOL

Common Name

English

PHENOL, O-METHOXY-

Systematic Name

English

O-HYDROXYANISOLE

Common Name

English

O-METHOXYPHENOL

Systematic Name

English

FEMA NO. 2532

Code

English

PYROGUAIAC ACID

Common Name

English

PYROCATECHOL MONOMETHYL ETHER

Systematic Name

English

GUAIASTIL

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29767