HinokitiolAn apoptosis inducer and potent metal chelator

Hinokitiol (CAS 499-44-5)

Hinokitiol | CAS 499-44-5 is rated 5.0 out of 5 by 1.
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Synonym: 4-Isopropyltropolone
Application: An apoptosis inducer and potent metal chelator
CAS Number: 499-44-5
Purity: ≥98%
Molecular Weight: 164.2
Molecular Formula: C10H12O2
* Refer to Certificate of Analysis for lot specific data (including water content).
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Hinokitol, an iron chelator originally extracted from woods of Thuja plicata and Chamaecyparis obtuse, has been found to inhibit ultraviolet B-induced apoptosis in keratinocytes of murine ear skin via antioxidant activity of metallothionein. Additionally, this compound has been found to also cause apoptotic cell death and cell cycle arrest of proliferating F9 cells via iron deprivation, resulting in an arrest at the G1-S interface or S phase. Antimicrobial activity has also been displayed by Hinokitiol through CPA (carboxypeptidase A) inhibition. Other studies have reported Hinokitiol to inhibit melanin synthesis by reducing protein levels of microphthalmia-associated transcription factor (MITF) and of Tyrosinase, a rate limiting melanogenic enzyme. Hinokitiol is an inhibitor of 12-LO.


References

1. Baba, T., et al. 1998. J. Invest. Dermatol.110: 24-28. PMID: 9424082
2. Inamori, Y., et al. 1999. Biol. Pharm. Bull. 22: 990-993. PMID: 10513629
3. Tanaka, T., et al. 1999. Cell Biol. Int. 23: 541-550. PMID: 10704238
4. Kim, D.S., et al. 2004. Arch. Pharm. Res. 27: 334-339. PMID: 15089040

Appearance :
Powder
Physical State :
Solid
Solubility :
Soluble in DMSO (up to 25 mg/ml), water (up to 25 mg/ml), ethanol, and ether.
Storage :
Store at room temperature
Melting Point :
≥ 260° C (lit.)
Boiling Point :
140° C (lit.) at 10 mmHg
Density :
1.13 g/cm3
Refractive Index :
1.553
IC50 :
Tyrosinase: IC50 = 90 nM (Agaricus bisporus ); BRCA1-associated RING domain protein 1: IC50 = 3890 nM (human); FM3A (Breast carcinoma cells): IC50 = 1100 nM (Mus musculus); p53-binding protein Mdm-2: IC50 = 3580 nM (human)
Ki Data :
Tyrosinase : Ki= 60 nM (Agaricus bisporus)
pK Values :
pKa: 7.06
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
GU4200000
PubChem CID :
3611
Merck Index :
14: 9390
MDL Number :
MFCD00040180
EC Number :
207-880-7
SMILES :
CC(C)C1=CC=CC(=O)C(O)=C1

Download SDS (MSDS)

Certificate of Analysis

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Rated 5 out of 5 by from Kim et al Kim et al. (PubMed ID 15089040) found that hinokitiol reduced the protein levels of MITF and of tyrosinase, thus reducing melanogenesis. -SCBT Publication Review
Date published: 2015-05-29
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