MedKoo Cat#: 145364 | Name: Pungenin

Description:

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

Pungenin is a glucoside. Pungenin is synthesized from 3,4-dihydroxyacetophenone by a short sequence involving manipulation of protecting groups on the 3 and 4 hydroxyl functions. Pungenin is a modest feeding deterrent for sixth-instar spruce budworm larvae, but it does not appear to retard the development of small larvae or lead to increased mortality.

Chemical Structure

Pungenin
Pungenin
CAS#55483-00-6

Theoretical Analysis

MedKoo Cat#: 145364

Name: Pungenin

CAS#: 55483-00-6

Chemical Formula: C14H18O8

Exact Mass: 314.1002

Molecular Weight: 314.29

Elemental Analysis: C, 53.50; H, 5.77; O, 40.72

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 #
No Data
Synonym
Pungenin;
IUPAC/Chemical Name
1-(4-hydroxy-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)ethan-1-one
InChi Key
AOXMCWFZPZRDPE-RKQHYHRCSA-N
InChi Code
1S/C14H18O8/c1-6(16)7-2-3-8(17)9(4-7)21-14-13(20)12(19)11(18)10(5-15)22-14/h2-4,10-15,17-20H,5H2,1H3/t10-,11-,12+,13-,14-/m1/s1
SMILES Code
CC(=O)C1=CC=C(O)C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C1
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 314.29 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: NEISH AC. Pungenin; a glucoside found in leaves of Picea pungens (Colorado spruce). Can J Biochem Physiol. 1957 Feb;35(2):161-7. PMID: 13404533. 2: Parent GJ, Méndez-Espinoza C, Giguère I, Mageroy MH, Charest M, Bauce É, Bohlmann J, MacKay JJ. Hydroxyacetophenone defenses in white spruce against spruce budworm. Evol Appl. 2019 Dec 20;13(1):62-75. doi: 10.1111/eva.12885. PMID: 31892944; PMCID: PMC6935585. 3: Gou P, Xiao Y, Lv L, Xie H. Hydroquinone and terpene glucosides from Leontopodium leontopodioides and their lipase inhibitory activity. Fitoterapia. 2018 Oct;130:89-93. doi: 10.1016/j.fitote.2018.08.010. Epub 2018 Aug 23. PMID: 30145331. 4: Mageroy MH, Jancsik S, Man Saint Yuen M, Fischer M, Withers SG, Paetz C, Schneider B, Mackay J, Bohlmann J. A Conifer UDP-Sugar Dependent Glycosyltransferase Contributes to Acetophenone Metabolism and Defense against Insects. Plant Physiol. 2017 Oct;175(2):641-651. doi: 10.1104/pp.17.00611. Epub 2017 Aug 9. PMID: 28794260; PMCID: PMC5619895. 5: Strunz GM, Giguère P, Thomas AW. Synthesis of pungenin, a foliar constituent of some spruce species, and investigation of its efficacy as a feeding deterrent for spruce budworm [Choristoneura fumiferana (Clem.)]. J Chem Ecol. 1986 Jan;12(1):251-60. doi: 10.1007/BF01045608. PMID: 24306414. 6: Mageroy MH, Lachance D, Jancsik S, Parent G, Séguin A, Mackay J, Bohlmann J. In vivo function of Pgβglu-1 in the release of acetophenones in white spruce. PeerJ. 2017 Jul 7;5:e3535. doi: 10.7717/peerj.3535. PMID: 28698822; PMCID: PMC5502087. 7: Taskova RM, Kokubun T, Garnock-Jones PJ, Jensen SR. Iridoid and phenylethanoid glycosides in the New Zealand sun hebes (Veronica; Plantaginaceae). Phytochemistry. 2012 May;77:209-17. doi: 10.1016/j.phytochem.2012.02.001. Epub 2012 Mar 1. PMID: 22386576. 8: Alblihy A. From desert flora to cancer therapy: systematic exploration of multi-pathway mechanisms using network pharmacology and molecular modeling approaches. Front Pharmacol. 2024 Apr 11;15:1345415. doi: 10.3389/fphar.2024.1345415. PMID: 38666020; PMCID: PMC11043532.