Wieland-gumlich aldehyde | 466-85-3 |chemical intermediate

MedKoo Cat#: 581536 | Name: Wieland-gumlich aldehyde

Description:

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

Wieland-Gumlich aldehyde is an indoline derived by chemical degradation from strychnine.

Chemical Structure

Wieland-gumlich aldehyde

CAS#466-85-3

Theoretical Analysis

MedKoo Cat#: 581536

Name: Wieland-gumlich aldehyde

CAS#: 466-85-3

Chemical Formula: C19H22N2O2

Exact Mass: 310.1681

Molecular Weight: 310.40

Elemental Analysis: C, 73.52; H, 7.14; N, 9.03; O, 10.31

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

Wieland-gumlich aldehyde; Caracurine VII; Deacetyldiaboline; Desacetyldiaboline

IUPAC/Chemical Name

(4bS,7aR,8aR,13R,13aR,13bS)-5,6,7a,8,8a,11,13,13a,13b,14-decahydro-7,9-methanooxepino[3,4-a]pyrrolo[2,3-d]carbazol-13-ol

InChi Key

UFUDXCDPABDFHK-IPAPBBTMSA-N

InChi Code

InChI=1S/C19H22N2O2/c22-18-16-12-9-15-19(6-7-21(15)10-11(12)5-8-23-18)13-3-1-2-4-14(13)20-17(16)19/h1-5,12,15-18,20,22H,6-10H2/t12-,15+,16+,17-,18+,19+/m0/s1

SMILES Code

C1C[C@@]23c4c(N[C@H]3[C@H]3[C@H]5C[C@H]2[N@@]1CC5=CCO[C@H]3O)cccc4

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

>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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 310.40 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: Sirasani G, Paul T, Dougherty W Jr, Kassel S, Andrade RB. Concise total syntheses of (+/-)-strychnine and (+/-)-akuammicine. J Org Chem. 2010 May 21;75(10):3529-32. doi: 10.1021/jo100516g. PubMed PMID: 20408591. 2: Jakubík J, Dolezal V. Determinants of positive cooperativity between strychnine-like allosteric modulators and N-methylscopolamine at muscarinic receptors. J Mol Neurosci. 2006;30(1-2):111-2. PubMed PMID: 17192652. 3: Jakubík J, Krejcí A, Dolezal V. Asparagine, valine, and threonine in the third extracellular loop of muscarinic receptor have essential roles in the positive cooperativity of strychnine-like allosteric modulators. J Pharmacol Exp Ther. 2005 May;313(2):688-96. Epub 2005 Jan 12. PubMed PMID: 15647330. 4: Wedig M, Novatchev N, Worch T, Laug S, Holzgrabe U. Evaluation of the impurity profile of alcuronium by means of capillary electrophoresis. J Pharm Biomed Anal. 2002 Jun 1;28(5):983-90. PubMed PMID: 12039641. 5: Sole D, Bonjoch J, Garcia-Rubio S, Peidro E, Bosch J. Enantioselective total synthesis of Wieland-Gumlich aldehyde and (-)-strychnine. Chemistry. 2000 Feb 18;6(4):655-65. PubMed PMID: 10807177. 6: Solé D, Bonjoch J, García-Rubio S, Peidró E, Bosch J. Total Synthesis of (-)-Strychnine via the Wieland-Gumlich Aldehyde. Angew Chem Int Ed Engl. 1999 Feb 1;38(3):395-397. doi: 10.1002/(SICI)1521-3773(19990201)38:3<395::AID-ANIE395>3.0.CO;2-5. PubMed PMID: 29711638. 7: Verpoorte R, Verzijl MJ, Svendsen AB. Further alkaloids from Strychnos dolichothyrsa. Planta Med. 1982 Jan;44(1):21-7. PubMed PMID: 17402076. 8: Verpoorte R, Svendsen AB. The alkaloids of Strychnos dolichothyrsa. Lloydia. 1976 Sep-Oct;39(5):357-62. PubMed PMID: 1018621.