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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Antibacterial activity of beta-thujaplicin.
T J Trust et al.
Canadian journal of microbiology, 19(11), 1341-1346 (1973-11-01)
Photophysical Spectral Features of fluorescent complexes on the basis of the novel ligand $\beta$-thujaplicin
Liu, Yang and Liu, et al.
Journal of Luminescence, 218, 116852-116852 (2020)
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)
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
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