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Indole-3-carboxaldehyde

CAS No.
487-89-8
Chemical Name:
Indole-3-carboxaldehyde
Synonyms
1H-INDOLE-3-CARBALDEHYDE;1h-indole-3-carboxaldehyde;3-FORMYLINDOLE;INDOLE-3-ALDEHYDE;INDOLE-3-CARBOXYALDEHYDE;INDOLE-3-CARBALDEHYDE;NSC 269470;INDOL-3-ALDEHYDE;3-Indolealdehyde;Indol-3-carbaldehyde
CBNumber:
CB0174846
Molecular Formula:
C9H7NO
Molecular Weight:
145.16
MDL Number:
MFCD00005622
MOL File:
487-89-8.mol
Last updated:2023-10-21 16:04:32

Indole-3-carboxaldehyde Properties

Melting point 193-198 °C(lit.)
Boiling point 264.27°C (rough estimate)
Density 1.1555 (rough estimate)
refractive index 1.4500 (estimate)
Flash point 240 °C
storage temp. Store below +30°C.
solubility DMSO (Slightly), Methanol (Slightly)
form Crystalline Powder
pka 15.50±0.30(Predicted)
color Off-white to beige-brown
Water Solubility Insoluble in water.
Sensitive Air Sensitive
BRN 114117
Stability Hygroscopic
LogP 1.680
CAS DataBase Reference 487-89-8(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 7FN04C32UO
NIST Chemistry Reference 3-Indole aldehyde(487-89-8)
EPA Substance Registry System 1H-Indole-3-carboxaldehyde (487-89-8)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS05,GHS07
Signal word  Danger
Hazard statements  H302-H314
Precautionary statements  P501-P260-P270-P264-P280-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405
Hazard Codes  Xi
Safety Statements  22-24/25
WGK Germany  3
RTECS  NL5993600
9-23
Autoignition Temperature >550 °C
Hazard Note  Irritant/Keep Cold
TSCA  Yes
HazardClass  IRRITANT
HS Code  29339990
NFPA 704
1
0 0

Indole-3-carboxaldehyde price More Price(38)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 129445 Indole-3-carboxaldehyde 97% 487-89-8 5g $37.1 2024-03-01 Buy
Sigma-Aldrich 8.04726 Indole-3-carbaldehyde for synthesis 487-89-8 25G $100 2024-03-01 Buy
Sigma-Aldrich 129445 Indole-3-carboxaldehyde 97% 487-89-8 25g $86.9 2024-03-01 Buy
TCI Chemical I0027 Indole-3-carboxaldehyde >98.0%(GC) 487-89-8 5g $36 2024-03-01 Buy
TCI Chemical I0027 Indole-3-carboxaldehyde >98.0%(GC) 487-89-8 25g $93 2024-03-01 Buy
Product number Packaging Price Buy
129445 5g $37.1 Buy
8.04726 25G $100 Buy
129445 25g $86.9 Buy
I0027 5g $36 Buy
I0027 25g $93 Buy

Indole-3-carboxaldehyde Chemical Properties,Uses,Production

Overview

1H-Indole-3-carboxaldehyde (I3C)(1a) is a natural compound that has been found in tomato seedlings, pea seedlings, barley, lupine, cabbage, and cotton[1]. Compound 1a has been isolated from etiolated pea seedlings playing an important role as a lateral bud growth inhibitor in the apical dominance of pea seedlings[2]. Besides occurring in nature, 1a can also be obtained synthetically[3]. The Vilsmeier–Haack formylation of indole is considered to be the most applicable method for the preparation of 1H-indole-3-carboxaldehyde (1a)[4]. 1H-Indole-3-carboxaldehyde(1a) represents an important building block of many natural and synthetic biologically active compounds, especially antitumor (camalexin, coscinamides), antidepressant (α-methyltryptamine), antimicrobial (phytoalexins: brassinin and cyclobrassinin), antiviral (chondramide A), anthelmintic (chondramide C), monoamine oxidase inhibitor(aplysinopin), antiplasmodial (isocryptolepine), antifungal (phytoalexins: caulilexins A–C), DNA replication and transcription inhibitor isocryptolepine, and muscle relaxant (α,β-cyclopiazonic acid) agents (Figure 1)[5-9].
the chemical structure of 1H-Indole-3-carboxaldehyde
Figure 1 the chemical structure of 1H-Indole-3-carboxaldehyde

Biosynthesis

Biosynthesis of natural 1H-indole-3-carboxaldehyde was first suggested by Tang and Bonner who reported that, aldehyde[1] was produced via biotransformation of indole-3acetic acid (IAA) using crude enzyme which is prepared from etiolated pea seedlings[10]. On the other hand, brassinin oxidase (BOLm; a fungal detoxifying enzyme) mediates the conversion of the phytoalexin brassinin into 1H-indole3-carboxaldehyde with equivalent ratio[11].
Also, bacteria play an important role in the biosynthesis of it via biotransformation of L-tryptophan using Escherichia coli[12]. 1H-Indole-3-carboxaldhyde and its derivatives are not only the key intermediates for the preparation of biologically active molecules as well indole alkaloids, but also they are important precursors for the synthesis of diverse heterocyclic derivatives.

Synthesis method

Previously, 1H-indole-3-carboxaldehyde has been prepared synthetically either via direct formylation of indole using e.g., Reimer-Tiemann reaction (aq. KOH/CHCl3)[13], Grignard reaction[14], Vilsmeier Haack reaction (POCl3/DMF)[15] or formylation of the potassium salt of indole using carbon monoxide under robust conditions of heat and pressure[16]. Sommelet reaction on gramine and on indole itself oxidation of N-skatyl-N-phenyl-hydroxylamine and/or by hydrolysis of 3-(1,3-dithiolan-2-yl) indole with boron trifluoride diethyl etherate BF3.O(C2H5)2 and mercury (II) oxide HgO.
Recently, the researchers developed general and simple approaches by the use of environmentally benign reagents in order to obtain 1H-indole-3-carboxaldyhde, for an example: Unusual oxidation of graminemethiodide [1-(1H-indol-3-yl)-N, N, N-trimethylmethanaminium iodide] using sodium nitrite in N, N-dimethylformamide (DMF) produces it in 68% yield[17]. For another method: Alkaline degradation of ascorbigen leads to a mixture of L-sorbose and L-tagatose derivatives. The later ketoses underwent acetylation and open ring of pyranose using acetic anhydride in pyridine in the presence of 4-dimethylaminopyridine (DMAP) leads to a mixture, which are separated by column chromatography. Deacetylations of compounds mixture have been accompanied by the formation of end product with yield (3%)[18].

Applications for the synthesis of bioactive indole alkaloids

Indole alkaloids constitute a large class of natural products and their diverse and complex structures have been attributed to potent biological activities such as anticancer, anti-inflammatory, antimicrobial, antimalarial, antiplasmodial and protein kinase inhibition. The isolation of bioactive compounds from natural sources is difficult, costly and an extremely time-consuming process, therefore synthetic pathways are more convenient than natural separation to deliver such compounds in considerable amounts. 1H-indole-3-carboxaldehyde is an effective precursor for the synthesis of bioactive indole alkaloids utilizing 1H-indole-3-carboxaldehyde and its derivatives.
Phytoalexins
Phytoalexins are secondary metabolites formed after plants have been exposed to stressful conditions. The formed compounds constitute an important defense against pathogenic microbes[19]. The common core structure of more than 20 isolated cruciferous phytoalexins is indole possessing a side chain or a heterocycle (fused or linked) containing one or two sulfur atoms[19, 20]. More than twenty phytoalexins have been identified in the family Cruciferae, occurring in many daily used edible vegetables. Chinese cabbage (brassinin, methoxybrassinin, cyclobrassinin, and methoxybrassitin), Japanese radish (brassitin and spirobrassinin), Japanese cabbage (methoxybrassenins A and B), Japanese kohlrabi (cyclobrassinone and methoxyspirobrassinin), Japanese false flax (camalexin) and Indian mustard (brassilexin) are examples of these vegetables[19, 20].
The isolation of indole phytoalexins from cruciferous plants does not provide sufficient quantities for biological screening. Hence, synthetic methods have been elaborated to prepare sufficient quantities of indole phytoalexins including brassinin, cyclobrassinin, brassitin, cyclobrassinone, brassilexin and (S)-(–)-spirobrassinin. A key intermediate in the synthesis of indole phytoalexins is 3-aminomethylindole, which is prepared from indole-3-carboxaldehyde.
Bis(indole) Alkaloids: Rhopaladines A–D
Four bis (indole) alkaloids, rhopaladines A–D, were isolated from the Okinawan marine tunicate Rhopalaea sp. Rhopaladin B exhibited inhibitory activity against cyclindependent kinase IV and c-ErbB-2 kinase. Rhopaladin C showed antibacterial activity against Sacina lutea and Corynebacterium xerosis[21] Rhopaladines C and D were prepared starting from indole-3-carboxaldehydes.
Coscinamides A and B
Coscinamides A and B are bis (indole)-containing marine natural products that were isolated from the marine sponge Coscinoderma sp. The preparation of coscinamides A and B started with the protection of 1H-indole-3-carboxaldehyde using Roush’s method[6].
Dipodazine, Isocryptolepine and Dipodazine was isolated and characterized as a major metabolite from Penicillium dipodomyis, and subsequently from meat-associated Penicillium nalgiovese[23]. Dipodazine was synthesized via a stereoselective aldol condensation from N-protected indole-3-carboxaldehyde 1b and 1,4diacetyl-2, 5-piperazinedione in the presence of cesium carbonate[24]. Despite the absence of any biological activity expressed by dipodazine, it has several analogues reported as being active as antifouling agents[22]. Isocryptolepine, an indoloquinoline alkaloid, was isolated from the West African plant Cryptolepis sanguinolenta[25]. The total synthesis of isocryptolepine via a photo-induced cyclization was reported in 2011[25]. The reaction of 1H-indole-3-carboxaldehyde (1a) with aniline in glacial acetic acid afforded the corresponding Schiff base, which is a key step.
Carbazole Alkaloids: Mukonine and Clausine E
The 1-oxygenated carbazole alkaloids (clausine E, mukonine, and koenoline) were isolated from higher plants of the Rutaceae family. Its synthesis involved an activation and intramolecular cyclization of monoester acids that were obtained via the reaction of 1H-indole-3-carboxaldehyde (1a) with dimethyl succinate and sodium hydride in methanol (Stobbe condensation)[26].

References

  1. Yannai, S. Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients; CRC Press: Boca Raton, 2003.
  2. Nakajima, E.; Nakano, H.; Yamada, K.; Shigemori, H.; Hasegawa, K. Phytochemistry 2002, 61, 863.
  3. El-Sawy, E.; Abo-Salem, H.; Mandour, A. Egypt. J. Chem. 2017, 60, 723.
  4. Philip, N. J.; Synder, H. R. Org. Synth. 1959, 39, 30.
  5. Dzurilla, M.; Kutschy, P.; Zaletova, J.; Ruzinsky, M.; Kovacik, V. Molecules 2001, 6, 716.
  6. Kuramochi, K.; Osada, Y.; Kitahara, T. Tetrahedron 2003, 59, 9447.
  7. Wang, Y. Y.; Chen, C. J. Chin. Chem. Soc. 2013, 54, 1363.
  8. (a) González-Lamothe, R.; Mitchell, G.; Gattuso, M.; Diarra, M. S.; Malouin, F.; Bouarab, K. Int. J. Mol. Sci. 2009, 10, 3400. (b) Burnett, J. C.; Rossi, J. J. Cell Chem. Biol. 2012, 19, 60.
  9. Herrmann, J.; Fayad, A. A.; Mu?ller, R. Nat. Prod. Rep. 2017, 34, 135.
  10. Tang Y. U. and Bonner J., The enzymatic inactivation of indole acetic acid. I. Some characteristics of the enzyme contained in pea seedlings, Arch Biochemistry, 13, 25 (1947).
  11. Pedras M. S. C., Minic Z. and Sarma-Mamillapalle V. K., Brassinin oxidase mediated transformation of the phytoalexin brassinin: Structure of the elusive co-product, deuterium isotope effect and stereoselectivity, Bioorganic of Medicinal Chemistry,19, 1390 (2011).
  12. Chi-Hsinchu H.-T. (TW), US Pat20130273617A1 (2013).
  13. Ellinger A. and Flamand C., About synthetically Obtained tryptophan and some of its derivatives, Hoppe-Seyler's, Zeitschrift fur Physiologische Chemie, 55, 8 (1908).
  14. British Pat. 618, 638 (1949) (Chem. Abst., 1949,
  15. Philip N.J. and Synder H.R., Indole-3-carboxaldhyde, Organic Synthesis, 39, 539 (1959).
  16. Tyson F.J. and Shaw J.T., A new approach to 3-indolecarboxaldehyde, Journal of American Chemical Society, 74, 2273 (1952).
  17. Sridar V., Maheswari R. and Reddy B. S. R.,An unusual oxidation of gramine methiodides under NaNO2/DMF conditionsIndian, Indian Journal of Chemistry (Section B), 40, 1253 (2001).
  18. Lavrenov S. N., Korolev A. M., Reznikova M. I., Sosnov A. V. and Preobrazhenskaya M. N., Study of 1-deoxy-1-(indol-3-yl)-L-sorbose,1deoxy-1-(indol-3-yl)-L-tagatose, and their analogs, Carbohydrate Research, 338, 143 (2003).
  19. Pedras, M. S. C.; Nycholat, C. M.; Montaut, S.; Xu, Y.; Khan, A. Q. Phytochemistry 2002, 59, 611.
  20. Pedras, M. S. C.; Yaya, E. E.; Glawischnig, E. Nat. Prod. Rep. 2011, 28, 1381.
  21. Janosik, T.; Johnson, A.-L.; Bergman, J. Tetrahedron 2002, 58, 2813.
  22. Kumar, R. N.; Suresh, T.; Mohan, P. S. Tetrahedron Lett. 2002, 43, 3327.
  23. Johnson, A.-L.; Janosik, T.; Bergman, J. ARKIVOC 2002, (viii), 57.
  24. Sjögren, M.; Johnson, A.-L.; Hedner, E.; Dahlström, M.; Göransson, U.; Shirani, H.; Bergman, J.; Jonsson, P. R.; Bohlin, L. Peptides 2006, 27, 2058.
  25. Hingane, D. G.; Kusurkar, R. S. Tetrahedron Lett. 2011, 52, 3686
  26. Budovská, M.; Kutschy, P.; Ko?ár, T.; Gondová, T.; Petrovaj, J. Tetrahedron 2013, 69, 1092.

Chemical Properties

?Indole-3-aldehyde [487-89-8], C9H7NO, Mr 145.16, mp 194 ℃, forms colorless crystals. It is readily soluble in ethanol and slightly soluble in cold water. It can be produced by Vilsmeier reaction of indole with formylmethylaniline or with dimethylformamide and phosphorus oxychloride. Indole-3-aldehyde can be used to make D,L-tryptophan and cyanine dyes.

Uses

Indole-3-carboxaldehyde is a biochemical used to prepare analogs of the indole phytoalexin cyclobrassinin with NR1R2 group. It was also used as the starting material for the synthesis of higher order indoles including isoindolo[2,1-a]indoles, aplysinopsins, and 4-substituted-tetrahydrobenz[cd]indoles.

Definition

ChEBI: A heteroarenecarbaldehyde that is indole in which the hydrogen at position 3 has been replaced by a formyl group.

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 1156, 1946 DOI: 10.1021/ja01211a006
The Journal of Organic Chemistry, 60, p. 7272, 1995 DOI: 10.1021/jo00127a036
Organic Syntheses, Coll. Vol. 4, p. 539, 1963

General Description

Indole-3-carboxaldehyde can undergo Schiff bases condensation to form multifunctional silica nano-vehicles and magnetic nanoparticles.

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View Lastest Price from Indole-3-carboxaldehyde manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Indole-3-carboxaldehyde pictures 2024-01-11 Indole-3-carboxaldehyde
487-89-8
US $122.00-1.00 / KG 1KG 99% g-kg-tons, free sample is available Henan Fengda Chemical Co., Ltd
Indole-3-carboxaldehyde pictures 2023-09-14 Indole-3-carboxaldehyde
487-89-8
US $100.00 / kgkg 1kgkg 0.99 100 Hebei Yanxi Chemical Co., Ltd.
Indole-3-carboxaldehyde pictures 2023-09-06 Indole-3-carboxaldehyde
487-89-8
US $0.00-0.00 / KG 50KG 99% 500000kg Hebei Guanlang Biotechnology Co., Ltd.
INDOLE-3-CARBOXALDEHYDE INDOLE-3-CARBOXYBENZALDEHYDE INDOLYL-3-ALDEHYDE I3CA AKOS BBS-00003214 3-Indolecarboxaldehyde beta-Indolylaldehyde b-Indolylaldehyde Indol-3-carbaldehyd Indol-3-carboxaldehyde 3-INDOLECARBALDEHYDE TIMTEC-BB SBB004120 3-Indole Carboxaldehyde Indole-3-Carboxaldehyde indoline-3-carbaldehyde Indolecarboxaldehyde Indole-3-Carboxaldehyde97% Indole-3-carboxaldehyde,99% 1H-Indole-3-carboxaldehyde (9CI) Indole-3-carboxaldehyde 96% AURORA KA-4265 LABOTEST-BB LT00937468 H-INDOLE-3-CARBOXALDEHYDE(9CI) INDOLE-3-CARBOXALDEHYDE (3-FORMYLINDOLE) 3-Indoledehyde INDOLE-3-ALDEHYDE (SEE 2722) Indole-3-methand 3-INDOLYLDEHYDE extrapure Indole-3-carboxaldehyde, 1H-: (3-Formylindole) Indole-3-carboxaldehyde ,98% INDOLE-3-CARBOXALDEHYDE(IAld) 1H-Indole-3-carboxaldehyde 96% 3-Formylindol 3-Formylindole Indole-3-aldehyde 1H-indole-3-carbaldehyde 3-Formyl-1H-indole Indole-3-aldehyde 3-Formylindole Indole-3-carboxaldeh INDOLE-3-CARBALDEHYDE FOR SYNTHESIS 3-Indolylformaldehyde NSC 10118 β-Indolylaldehyde e-3-carboxaL Indol-3-Aldegid Tropisetron Hydrochloride Impurit Ⅱ:Indole-3-carboxaldehyde Indole-3-Carboxaldehyde in stock Factory 2-ACETAMIDO-,METHYLESTER,MONOPICRATE Indole-3-carboxaldehyde> Indole-3-carboxaldehyde, 98%, for synthesis Indole-3-carboxaldehyde 3-Formylindole 3-Indolylformaldehyde Indole-3-aldehyde Indole-3-formaldehyde Indole-3-carboxaldehyde ISO 9001:2015 REACH Indole-3-carboxaldehyde ethyl Tropisetron Hydrochloride Impurit Ⅱ:Indole-3-carboxaldehyde 3-Indolylaldehyde extrapure, 99% NSC269470 NSC-269470 INDOL-3-ALDEHYDE INDOLE-3-ALDEHYDE INDOLE-3-CARBALDEHYDE INDOLE-3-CARBOXYALDEHYDE