MedKoo Cat#: 596345 | Name: Juvabione

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Juvabione, historically known as the paper factor, is the methyl ester of todomatuic acid, both of which are sesquiterpenes (C15) found in the wood of true firs of the genus Abies. They occur naturally as part of a mixture of sesquiterpenes based upon the bisabolane scaffold. Sesquiterpenes of this family are known as insect juvenile hormone analogues (IJHA) because of their ability to mimic juvenile activity in order to stifle insect reproduction and growth. These compounds play important roles in conifers as the second line of defense against insect induced trauma and fungal pathogens.

Chemical Structure

Juvabione
Juvabione
CAS#17904-23-3

Theoretical Analysis

MedKoo Cat#: 596345

Name: Juvabione

CAS#: 17904-23-3

Chemical Formula: C19H32O3

Exact Mass: 308.2351

Molecular Weight: 308.46

Elemental Analysis: C, 73.98; H, 10.46; O, 15.56

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Juvabione;
IUPAC/Chemical Name
(3S,4aS,6aS,7R,10aS,10bR)-7-(hydroxymethyl)-3,4a,7,10a-tetramethyldodecahydro-1H-benzo[f]chromene-3-carbaldehyde
InChi Key
NSZDQEHQKYPHIG-SVMUCYCZSA-N
InChi Code
InChI=1S/C19H32O3/c1-16(12-20)8-5-9-18(3)14(16)7-11-19(4)15(18)6-10-17(2,13-21)22-19/h13-15,20H,5-12H2,1-4H3/t14-,15-,16+,17+,18+,19+/m1/s1
SMILES Code
O=C[C@](C)(CC1)O[C@]2(C)[C@H]1[C@@]3(C)CCC[C@](CO)(C)[C@H]3CC2
Appearance
Solid powder
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
>2 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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 308.46 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.

Recalculate based on batch purity %
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: Awasthi P, Sharma P. In silico screening of the juvabione category of juvenile hormone analogues with juvenile hormone binding protein of Galleria mellonella--a docking study. SAR QSAR Environ Res. 2012 Oct;23(7-8):607-25. doi: 10.1080/1062936X.2012.665384. Epub 2012 Jul 17. PubMed PMID: 22799597. 2: Jedlicka P, Hrdý I, Kuldová J, Wimmer Z. The systemic effects of juvenoids on the red firebug Pyrrhocoris apterus and on the pea aphid Acyrthosiphon pisum with data on life table response. Pest Manag Sci. 2007 Oct;63(10):1026-35. PubMed PMID: 17724791. 3: Itagaki N, Iwabuchi Y. Enantio- and diastereo-controlled synthesis of (+)-juvabione employing organocatalytic desymmetrization and photoinduced fragmentation. Chem Commun (Camb). 2007 Mar 12;(11):1175-6. Epub 2007 Jan 9. PubMed PMID: 17347730. 4: Pearson AJ, Paramahamsan H, Dudones JD. Vicinal stereocontrol during nucleophilic addition to arene chromium tricarbonyl complexes: formal synthesis of (+/-)-erythro Juvabione. Org Lett. 2004 Jun 24;6(13):2121-4. PubMed PMID: 15200300. 5: Fine PM, Cass GR, Simoneit BR. Chemical characterization of fine particle emissions from fireplace combustion of woods grown in the northeastern United States. Environ Sci Technol. 2001 Jul 1;35(13):2665-75. PubMed PMID: 11452590. 6: Bergner EJ, Helmchen G. Enantioselective synthesis of (+)-juvabione. J Org Chem. 2000 Aug 11;65(16):5072-4. PubMed PMID: 10956500. 7: Bohlmann J, Crock J, Jetter R, Croteau R. Terpenoid-based defenses in conifers: cDNA cloning, characterization, and functional expression of wound-inducible (E)-alpha-bisabolene synthase from grand fir (Abies grandis). Proc Natl Acad Sci U S A. 1998 Jun 9;95(12):6756-61. PubMed PMID: 9618485; PubMed Central PMCID: PMC22624. 8: Bowers WS. Insect-plant interactions: endocrine defences. Ciba Found Symp. 1984;102:119-37. PubMed PMID: 6559111. 9: Zaoral M, Sláma K. Peptides with juvenile hormone activity. Science. 1970 Oct 2;170(3953):92-3. PubMed PMID: 5452900.