Synonym
Chicanine; Chicanin;
IUPAC/Chemical Name
4-((2R,3S,4R,5R)-5-(benzo[d][1,3]dioxol-5-yl)-3,4-dimethyltetrahydrofuran-2-yl)-2-methoxyphenol
InChi Key
JPDORDSJPIKURD-OCBHBYCGSA-N
InChi Code
InChI=1S/C20H22O5/c1-11-12(2)20(14-5-7-16-18(9-14)24-10-23-16)25-19(11)13-4-6-15(21)17(8-13)22-3/h4-9,11-12,19-21H,10H2,1-3H3/t11-,12+,19+,20+/m0/s1
SMILES Code
OC1=CC=C([C@@H]2O[C@@H](C3=CC=C(OCO4)C4=C3)[C@H](C)[C@@H]2C)C=C1OC
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
342.39
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Choi H, Han J, Choi J, Lee K. Divergent Syntheses of (-)-Chicanine,
(+)-Fragransin A2, (+)-Galbelgin, (+)-Talaumidin, and (+)-Galbacin
via One-Pot Homologative γ-Butyrolactonization. Molecules. 2024 Feb
2;29(3):701. doi: 10.3390/molecules29030701. PMID: 38338445; PMCID: PMC10856021.
2: Chen H, Sohn J, Zhang L, Tian J, Chen S, Bjeldanes LF. Anti-inflammatory
effects of chicanine on murine macrophage by down-regulating LPS-induced
inflammatory cytokines in IκBα/MAPK/ERK signaling pathways. Eur J Pharmacol.
2014 Feb 5;724:168-74. doi: 10.1016/j.ejphar.2013.12.016. Epub 2013 Dec 18.
PMID: 24361309; PMCID: PMC3970222.
3: Xia T, Ma J, Sun Y, Sun Y. Androgen receptor suppresses inflammatory response
of airway epithelial cells in allergic asthma through MAPK1 and MAPK14. Hum Exp
Toxicol. 2022 Jan-Dec;41:9603271221121320. doi: 10.1177/09603271221121320. PMID:
35982617.
4: Sadhu SK, Okuyama E, Fujimoto H, Ishibashi M. Separation of Leucas aspera, a
medicinal plant of Bangladesh, guided by prostaglandin inhibitory and
antioxidant activities. Chem Pharm Bull (Tokyo). 2003 May;51(5):595-8. doi:
10.1248/cpb.51.595. PMID: 12736464.
5: Yin W, Liu JQ, Zhang GS. [Chemical constituents of Osmanthus fragrans
fruits]. Zhongguo Zhong Yao Za Zhi. 2013 Dec;38(24):4329-34. Chinese. PMID:
24791540.
6: Song W. [Quality of Schisandra incarnata Stapf]. Zhongguo Zhong Yao Za Zhi.
1991 Apr;16(4):204-6, 253. Chinese. PMID: 1863329.
