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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 of GUAIAZULENE

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
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

Šorm, F.|Zaoral, M.|Herout, V.
1
Curator's Comment: Isolation from chamomile oil.

Approval Year

2018
436
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
 9.8 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
ANZUWEI

Approved Use

It is usually used in the treatment of gastric ulcer.

Launch Date

1976
Primary
Approved
8429
ANZUWEI

Approved Use

It is usually used in the treatment of gastritis.

Launch Date

1976
Primary
Approved
8429
Ophthalmo-Azulen

Approved Use

It has been used for ocular burns and corneal burns.
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

PubMed

TitleDatePubMed
Synthesis of new azulene derivatives and study of their effect on lipid peroxidation and lipoxygenase activity.
2002 Jul
Intraindividual comparison of two different skin care conceptions in patients undergoing radiotherapy of the head-and-neck region. Creme or powder?
2002 Jun
Determination of the temperature dependence of water solubilities of polycyclic aromatic hydrocarbons by a generator column-on-line solid-phase extraction-liquid chromatographic method.
2002 Jun
Synthesis and antioxidant activity of 3-substituted guaiazulene derivatives.
2002 Jun
Solvatochromism, halochromism, and preferential solvation of new dipolar guaiazulenyl 1,4-benzoquinone methides.
2003 Apr 21
Photomutagenicity of cosmetic ingredient chemicals azulene and guaiazulene.
2003 Sep 29
Reaction of a terminal phosphinidene complex with azulenes: eta1-complexes, C--H bond insertions, and 1,4-adducts.
2004 Jun 7
Optimisation of stir bar sorptive extraction and liquid desorption combined with large volume injection-gas chromatography-quadrupole mass spectrometry for the determination of volatile compounds in wines.
2008 Aug 22
Guaiazulene in health care products: determination by GC-MS and HPLC-DAD and photostability test.
2008 Aug 5
Enhancement of Escherichia coli and Staphylococcus aureus antibiotic susceptibility using sesquiterpenoids.
2008 Nov
Study on the photostability of guaiazulene by high-performance liquid chromatography/mass spectrometry and gas chromatography/mass spectrometry.
2008 Sep
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
Patents

Patents

US2734931 A
1
US4755529 A
1

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Ophthalmic ointment in adults and children apply into the conjunctival sac or applied to the skin of the eyelids and around the eye 3 - 5 times per day until complete healing. Without consulting a doctor, do not use the medicine for longer than 10 days. https://pribalovy-letak.info/ophthalmo-azulen
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
  • Download
Name Type Language
GUAIAZULENE
INCI   MART.   MI   WHO-DD  
INCI  
Official Name English
7-ISOPROPYL-1,4-DIMETHYLAZULENE
Systematic Name English
1,4-DIMETHYL-7-ISOPROPYLAZULENE
JAN  
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
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
WHO-VATC QS01XA01
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
Code System Code Type Description
EVMPD
SUB14032MIG
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PRIMARY
ChEMBL
CHEMBL1408759
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PRIMARY
SMS_ID
100000092369
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PRIMARY
PUBCHEM
3515
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PRIMARY
DRUG BANK
DB13329
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PRIMARY
NSC
4714
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PRIMARY
DAILYMED
2OZ1K9JKQC
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PRIMARY
CAS
489-84-9
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PRIMARY
MESH
C004451
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PRIMARY
MERCK INDEX
m5860
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PRIMARY Merck Index
EPA CompTox
DTXSID7045996
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PRIMARY
WIKIPEDIA
GUAIAZULENE
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
PRIMARY
FDA UNII
2OZ1K9JKQC
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PRIMARY
RXCUI
26290
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PRIMARY RxNorm
DRUG CENTRAL
3272
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PRIMARY
ECHA (EC/EINECS)
207-701-2
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
PRIMARY
CHEBI
5550
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
PRIMARY
Related Record Type Details
Structure of GUAIAZULENE
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