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469521

Sigma-Aldrich

β-Thujaplicin

99%

Synonym(s):

beta-Thujaplicin, 2-Hydroxy-4-isopropyl-2,4,6-cycloheptatrien-1-one, Hinokitiol

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About This Item

Empirical Formula (Hill Notation):
C10H12O2
CAS Number:
499-44-5
Molecular Weight:
164.20
EC Number:
207-880-7
MDL number:
MFCD00040180
UNSPSC Code:
12352100
PubChem Substance ID:
24870612
NACRES:
NA.22

Quality Level

100

Assay

99%

bp

140 °C/10 mmHg (lit.)

mp

50-52 °C (lit.)

SMILES string

CC(C)C1=CC=CC(=O)C(O)=C1

InChI

1S/C10H12O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-7H,1-2H3,(H,11,12)

InChI key

FUWUEFKEXZQKKA-UHFFFAOYSA-N

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General description

β-Thujaplicin is a monoterpene and tropolonecompound having unique conjugated seven-membered ring. Thujaplicins arerecognized as isomers of isopropyl tropolones. Additionally it is a fluorescentligand used for the synthesis of lanthanide organic complexes.

Application


  • Fabrication and characterization of sodium alginate/blueberry anthocyanins/hinokitiol loaded ZIF-8 nanoparticles composite films with antibacterial activity for monitoring pork freshness.: This study develops composite films incorporating hinokitiol for its antibacterial properties to monitor pork freshness, highlighting its potential in food safety applications (Guo et al., 2024).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A novel synthetic pathway for tropolone ring formation via the olefin monoterpene intermediate terpinolene in cultured Cupressus lusitanica cells
Fujita, Koki and Bunyu, et al.
Journal of Plant Physiology, 171, 610-614 (2014)
J Zhao et al.
Applied microbiology and biotechnology, 55(3), 301-305 (2001-05-09)
Production of a novel antimicrobial tropolone, beta-thujaplicin, in Cupressus lusitanica suspension cultures was studied by using a variety of chemicals and fungal elicitors. Sodium alginate, chitin, and methyl jasmonate resulted in 2-, 2.5-, and 3-fold higher beta-thujaplicin production, respectively, than
Jian Zhao et al.
Journal of experimental botany, 54(383), 647-656 (2003-01-30)
The biosynthesis of a phytoalexin, beta-thujaplicin, in Cupressus lusitanica cell cultures can be stimulated by a yeast elicitor, H(2)O(2), or methyl jasmonate. Lipoxygenase activity was also stimulated by these treatments, suggesting that the oxidative burst and jasmonate pathway may mediate
Yaeno Arima et al.
The Journal of antimicrobial chemotherapy, 51(1), 113-122 (2002-12-21)
Beta-thujaplicin (hinokitiol) is a tropolone-related compound purified from the wood of Chamaecyparis obtusa, SIEB: et Zucc. and Thuja plicata D. Don. All Staphylococcus aureus isolates were inhibited by beta-thujaplicin with MICs of 1.56-3.13 mg/L. However, a paradoxical zone phenomenon occurred
Synthesis of naturally occurring tropones and tropolones
Liu, Na and Song, et al.
Tetrahedron, 70, 9281-9305 (2014)
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