File:Gamma-thujaplicin.png · Wikimedia Commons · See Wikimedia Commons
β-thujaplicin
Sign in to saveAlso known as Hinokitiol, 4-Isopropyltropolone
Hinokitiol (β-thujaplicin) is a natural monoterpenoid found in the wood of trees in the family Cupressaceae. It is a tropolone derivative and one of the thujaplicins. Hinokitiol is used in oral and skin care products, and is a food additive used in Japan.
OverviewAI-generated
β-thujaplicin is a chemical compound with the formula C₁₀H₁₂O₂. Its IUPAC name is 2-hydroxy-6-propan-2-ylcyclohepta-2,4,6-trien-1-one. The substance has a mass of 164.08373 and a weight of 164.20. It possesses a charge of 0, an xlogp value of 2.1, and a topological polar surface area of 37.3. The molecule contains one hydrogen bond donor and two hydrogen bond acceptors.
The compound is associated with 257 PubMed entries and is referenced by 95 other encyclopedia articles. Its canonical SMILES notation is CC(C)C1=CC(=O)C(=CC=C1)O.
Synthesized by Vinony from 16 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Chemical data
- Formula
- C10H12O2
- Molecular weight
- 164.2 g/mol
- IUPAC name
- 2-hydroxy-6-propan-2-ylcyclohepta-2,4,6-trien-1-one
- SMILES
- CC(C)C1=CC(=O)C(=CC=C1)O
- InChIKey
- FUWUEFKEXZQKKA-UHFFFAOYSA-N
- XLogP
- 2.1
- Polar surface area
- 37.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
257 papers- Hinokitiol ameliorates MASH in mice by therapeutic targeting of hepatic Nrf2 and inhibiting hepatocyte ferroptosis.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2025
- [Synergistic effect of β-thujaplicin and tigecycline against tet(X4)-positive Escherichia coli in vitro].Sheng wu gong cheng xue bao = Chinese journal of biotechnology · 2023
- β-Thujaplicin modulates estrogen receptor signaling and inhibits proliferation of human breast cancer cells.Bioscience, biotechnology, and biochemistry · 2015
- Preventive effects of β-thujaplicin against UVB-induced MMP-1 and MMP-3 mRNA expressions in skin fibroblasts.The American journal of Chinese medicine · 2012
- β-Thujaplicin inhibits basal-like mammary tumor growth by regulating glycogen synthase kinase-3β/β-catenin signaling.Food & function · 2019
via PubMed
~11 min read
Encyclopedic overview
18 sectionsContents
- History
- Natural occurrence
- Chemical synthesis
- Chemistry
- Ionophore
- Biological properties
- Safety
- Uses
- Skin and oral care products
- Insect repellent
- Food preservative
- Wood preservative
- Research directions
- Iron transport
- Cancer research
- See also
- References
- External links
Hinokitiol (β-thujaplicin) is a natural monoterpenoid found in the wood of trees in the family Cupressaceae. It is a tropolone derivative and one of the thujaplicins. Hinokitiol is used in oral and skin care products, and is a food additive used in Japan.
== History == Hinokitiol was discovered by a Japanese chemist Tetsuo Nozoe in 1936. It was isolated from the essential oil component of the heartwood Taiwanese hinoki, from which the compound ultimately adopted its name. Hinokitiol is the first non-benzenoid aromatic compound identified. The compound has a heptagonal molecular structure and was first synthesized by Ralph Raphael in 1951. Due to its iron-chelating activity, hinokitiol has been called an "Iron Man molecule" in the scientific media, which is ironic because Tetsuo is translated into English as "Iron Man". Taiwanese hinoki is native to East Asian countries, particularly to Japan and Taiwan. Hinokitiol has also been found in other trees of the Cupressaceae family, including Thuja plicata Donn ex D. Don which is common in the Pacific Northwest.
Excerpted from Wikipedia’s “β-thujaplicin” article, available under the CC BY-SA 4.0 licence.