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Guaiol

CAT: 0804-HY-N3980-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-N3980-02Size:10 mM - 1 mL
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Guaiol is a sesquiterpenoid alcohol with oral activity found in various traditional Chinese medicines, exhibiting biological activities such as anti-proliferative, autophagy-promoting, insecticidal, anti-anxiety, anti-inflammatory, diuretic, and blood pressure-lowering effects. Guaiol induces apoptosis in non-small cell lung cancer cells by regulating the stability of RAD51 through autophagy modulation. Guaiol can also act directly on parasites, inhibiting their growth by affecting the kinetoplast, mitochondrial matrix and plasma membrane of the promastigotes. Guaiol kills amastigotes at an IC50 of 0.01 µg/mL. Guaiol can be used in research related to cancer, infections, cardiovascular diseases, and inflammatory conditions[1][2][3][4][5][6].
CAS Number
489-86-1
Product Name Alternative
Champacol; Guaiac alcohol
UNSPSC
12352211
Hazard Statement
H302, H315, H319, H335
Target
Autophagy; RAD51
Type
Natural Products
Related Pathways
Autophagy; Cell Cycle/DNA Damage
Applications
COVID-19-immunoregulation
Field of Research
Cancer; Infection; Inflammation/Immunology; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/guaiol.html
Purity
99.67
Solubility
DMSO : 33.33 mg/mL (ultrasonic)
Smiles
C[C@@H]1C2=C([C@H](CC[C@@H](C(C)(O)C)C2)C)CC1
Molecular Formula
C15H26O
Molecular Weight
222.37
Precautions
H302, H315, H319, H335
References & Citations
[1]Yang, Q, et al. (−) -Guaiol regulates RAD51 stability via autophagy to induce cell apoptosis in non-small cell lung cancer Oncotarget. 2016 Sep 20;7 (38) :62585-62597.|[2]Ali, A., Tabanca, et al. Chemical composition and biological activity of four salvia essential oils and individual compounds against two species of mosquitoes J. Agric. Food Chem. 63 (2), 447-456 (2015) .|[3]Liu, T, et al. Guaiol - a naturally occurring insecticidal sesquiterpene Nat. Prod. Commun. 8 (10), 1353-1354 (2013) .|[4]Garcia M C F, et al. The in vitro antileishmanial activity of essential oil from Aloysia gratissima and guaiol, its major sesquiterpene against Leishmania amazonensis[J]. Parasitology, 2018, 145 (9) : 1219-1227.|[5]Thurman E M. Analysis of terpenes in hemp (Cannabis sativa) by gas chromatography/mass spectrometry: Isomer identification analysis[M]//Comprehensive Analytical Chemistry. Elsevier, 2020, 90: 197-233.|[6]Yang M, et al. Determination and pharmacokinetic study of guaiol in rat plasma by gas chromatography–mass spectrometry with selected ion monitoring[J]. Journal of Chromatography B, 2018, 1085: 30-35.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C, 3 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Guaiol

Guaiol is a guaiane sesquiterpenoid.

CAS Number489-86-1
PubChem CID227829
IUPAC Name2-[(3S,5R,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol
Molecular FormulaC15H26O
Molecular Weight222.37
XLogP3.1
Topological Polar Surface Area20.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count1
Heavy Atom Count16
Formal Charge0
Complexity301
SMILES
C[C@H]1CC[C@H](CC2=C1CC[C@@H]2C)C(C)(C)O
InChI
InChI=1S/C15H26O/c1-10-5-7-12(15(3,4)16)9-14-11(2)6-8-13(10)14/h10-12,16H,5-9H2,1-4H3/t10-,11-,12+/m0/s1
InChIKey
TWVJWDMOZJXUID-SDDRHHMPSA-N
Chemical Structure
2D Structure
2D structure of Guaiol
CAS: 489-86-1
CID: 227829
Formula: C15H26O
MW: 222.37
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight222.37
XLogP33.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count1
Exact Mass222.198365449
Monoisotopic Mass222.198365449
Topological Polar Surface Area20.2 Ų
Heavy Atom Count16
Formal Charge0
Complexity301
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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