Synonym
(+/-)-Ascaridole; (Z)-Ascaridole; Ascarisin; Askaridol; Ascaridole; Ascaridole, (+/-)-; Boldo ascaridole
IUPAC/Chemical Name
(1S,4S)-1-isopropyl-4-methyl-2,3-dioxabicyclo[2.2.2]oct-5-ene
InChi Key
MGYMHQJELJYRQS-ZJUUUORDSA-N
InChi Code
InChI=1S/C10H16O2/c1-8(2)10-6-4-9(3,5-7-10)11-12-10/h4,6,8H,5,7H2,1-3H3/t9-,10+/m1/s1
SMILES Code
CC(C)[C@]12CC[C@@](C)(C=C2)OO1
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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
168.24
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. Geroldinger G, Tonner M, Hettegger H, Bacher M, Monzote L, Walter M, Staniek K, Rosenau T, Gille L. Mechanism of ascaridole activation in Leishmania. Biochem Pharmacol. 2017 May 15;132:48-62. doi: 10.1016/j.bcp.2017.02.023. Epub 2017 Mar 2. PMID: 28263719.
2. Monzote L, Geroldinger G, Tonner M, Scull R, De Sarkar S, Bergmann S, Bacher M, Staniek K, Chatterjee M, Rosenau T, Gille L. Interaction of ascaridole, carvacrol, and caryophyllene oxide from essential oil of Chenopodium ambrosioides L. with mitochondria in Leishmania and other eukaryotes. Phytother Res. 2018 Sep;32(9):1729-1740. doi: 10.1002/ptr.6097. Epub 2018 Apr 19. PMID: 29672979; PMCID: PMC6208284.
3. Sahli F, Sousa MSE, Vileno B, Lichter J, Lepoittevin JP, Blömeke B, Giménez-Arnau E. Understanding the skin sensitization capacity of ascaridole: a combined study of chemical reactivity and activation of the innate immune system (dendritic cells) in the epidermal environment. Arch Toxicol. 2019 May;93(5):1337-1347. doi: 10.1007/s00204-019-02444-3. Epub 2019 Apr 16. PMID: 30993377.