GUAIAZULENE

First approved in 2018

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H18
Molecular Weight	198.3034
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1

InChI

InChIKey=FWKQNCXZGNBPFD-UHFFFAOYSA-N

InChI=1S/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H3

HIDE SMILES / InChI

Molecular Formula	C15H18
Molecular Weight	198.3034
Charge	0
Count

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

Description
Sources: http://www.cosmeticsinfo.org/ingredient/guaiazulene-0
Curator's Comment: description was created based on several sources, including: https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=73.2180 https://www.ncbi.nlm.nih.gov/pubmed/26401381

Guaiazulene is a blue compound. It is a derivative of azulene, guaiazulene is a bicyclic sesquiterpene that is a constituent of some essential oils, mainly oil of guaiac and chamomile oil. Guaiazulene is an U.S. FDA-approved cosmetic color additive. Guaiazulene is used in the formulation of bath products, cleansing products, depilatories, hair bleaches, hair conditioners, hair dyes and colors, hair straighteners, permanent waves, skin care products and skin fresheners. Guaiazulene has antioxidant, antifungal, antimicrobial, anti-inflammatory, anti-spasmodic, anti-ulcer, antitumoral activities and relaxant properties. Common side effects are: iarrhea, constipation, etc.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 1A2 72 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9112807	Inhibitor 8297
Cytochrome P450 1A1 31 Target ID: CHEMBL2231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9112807	Inhibitor 8297
Cytochrome P450 2B6 19 Target ID: CHEMBL4729 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9112807	Inhibitor 8297
lipid oxidation 20 Target ID: GO:0034440 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9306266	Inhibitor 8297	9.8 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Gastric ulcer 67 Sources: http://www.120ty.net/bencandy.php?fid=141&id=43550	Primary	Approved 8429	ANZUWEI Approved Use It is usually used in the treatment of gastric ulcer. Launch Date 1976
Gastritis 45 Sources: http://www.120ty.net/bencandy.php?fid=141&id=43550	Primary	Approved 8429	ANZUWEI Approved Use It is usually used in the treatment of gastritis. Launch Date 1976
Corneal burns 1 Sources: https://pribalovy-letak.info/ophthalmo-azulen	Primary	Approved 8429	Ophthalmo-Azulen Approved Use It has been used for ocular burns and corneal burns.
Eyelids, conjunctiva and cornea injuries 1 Sources: https://pribalovy-letak.info/ophthalmo-azulen	Primary	Approved 8429	Ophthalmo-Azulen Approved Use Ophthalmo-Azulen is used in adults and children for eyelids, conjunctiva and cornea injure treatment, to accelerate the healing process after removing foreign bodies from the cornea.

PubMed

Title	Date	PubMed
[Use of garmastan in the prophylaxis and therapy of sore nipples of the breast].	2001	11803878
Synthesis of new azulene derivatives and study of their effect on lipid peroxidation and lipoxygenase activity.	2002 Jul	12130848
Synthesis and antioxidant activity of 3-substituted guaiazulene derivatives.	2002 Jun	12049221
Torilin from Torilis japonica, as a new inhibitor of testosterone 5 alpha-reductase.	2003 May	12802730
Temperature dependence of the infinite dilution activity coefficient and Henry's law constant of polycyclic aromatic hydrocarbons in water.	2004 Aug	15212897
Guaiazulene in health care products: determination by GC-MS and HPLC-DAD and photostability test.	2008 Aug 5	18395389
Benzo[cd]azulene skeleton: azulene, heptafulvene, and tropone derivatives.	2009 Dec 3	19904921
Quantification approach for assessment of sparkling wine volatiles from different soils, ripening stages, and varieties by stir bar sorptive extraction with liquid desorption.	2009 Mar 9	19216881
Effect of Matricaria chamomilla L. flower essential oil on the growth and ultrastructure of Aspergillus niger van Tieghem.	2010 May 15	20385420
Cytotoxic activity of guaiazulene on gingival fibroblasts and the influence of light exposure on guaiazulene-induced cell death.	2011 Feb	20854889

Patents

Sample Use Guides

In Vivo Use Guide

Take 1 tablet (2 mg of the active ingredient) at a time, three times daily, before meals.

Route of Administration: Other

In Vitro Use Guide

Guaiazulene caused statistically important increases in total oxidative stress levels at concentrations higher than 100 µg/mL in rat neuron cell line.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:19:29 GMT 2023` Edited by `admin` on `Fri Dec 15 16:19:29 GMT 2023`
Record UNII	2OZ1K9JKQC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GUAIAZULENE

Official Name

English

7-ISOPROPYL-1,4-DIMETHYLAZULENE

Systematic Name

English

1,4-DIMETHYL-7-ISOPROPYLAZULENE

Systematic Name

English

KESSAZULEN

Common Name

English

GUAIAZULENE (CONSTITUENT OF CHAMOMILE) [DSC]

Common Name

English

GUAIAZULENE [MART.]

Common Name

English

UROAZULEN

Common Name

English

S-GUAIAZULENE

Common Name

English

NSC-4714

Code

English

VAUMIGAN

Common Name

English

Guaiazulene [WHO-DD]

Common Name

English

GUAIAZULENE [MI]

Common Name

English

VETIVAZULEN

Common Name

English

GUAIAZULEN

Common Name

English

PURAZULEN

Common Name

English

SILAZULON

Common Name

English

1,4-DIMETHYL-7-ISOPROPYL-AZULENE

Systematic Name

English

GUAIAZULENE [INCI]

Common Name

English

AZULENE, 1,4-DIMETHYL-7-(1-METHYLETHYL)-

Systematic Name

English

1,4-DIMETHYL-7-ISOPROPYLAZULENE [JAN]

Common Name

English

Classification Tree Code System Code

WHO-ATC

S01XA01