Juvabione

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MedKoo CAT#: 596345

CAS#: 17904-23-3

Description: 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

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Juvabione
CAS# 17904-23-3
Instruction

Theoretical Analysis

MedKoo Cat#: 596345
Name: Juvabione
CAS#: 17904-23-3
Chemical Formula: C19H32O3
Exact Mass: 308.24
Molecular Weight: 308.460
Elemental Analysis: C, 73.98; H, 10.46; O, 15.56

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.