Indol

Bezeichnung:Indol

CAS-Nr120-72-9

Englisch Name:Indole

CBNumberCB8275772

SummenformelC8H7N

Molgewicht117.15

MOL-Datei120-72-9.mol

Synonyma

Indol

Indol physikalisch-chemischer Eigenschaften

Schmelzpunkt	51-54 °C (lit.)
Siedepunkt	253-254 °C (lit.)
Dichte	1.22
Dampfdruck	0.016 hPa (25 °C)
Brechungsindex	1.6300
FEMA	2593 \| INDOLE
Flammpunkt	>230 °F
storage temp.	2-8°C
Löslichkeit	methanol: 0.1 g/mL, clear
pka	3.17 (quoted, Sangster, 1989)
Aggregatzustand	Crystalline Powder
Farbe	White to slightly pink
PH	5.9 (1000g/l, H2O, 20℃)
Geruch (Odor)	fecal odor, floral in high dilution
Odor Threshold	0.0003ppm
Geruchsart	animal
Wasserlöslichkeit	2.80 g/L (25 ºC)
Sensitive	Light Sensitive
Merck	14,4963
JECFA Number	1301
BRN	107693
Stabilität	Stable, but may be light or air sensitive. Incompatible with strong oxidizing agents, iron and iron salts.
LogP	2.14-2.24
CAS Datenbank	120-72-9(CAS DataBase Reference)
NIST chemische Informationen	Indole(120-72-9)
EPA chemische Informationen	Indole (120-72-9)

Sicherheit

Kennzeichnung gefährlicher	Xn,N,T
R-Sätze:	21/22-37/38-41-50/53-36-39/23/24/25-23/24/25-52/53
S-Sätze:	26-36/37/39-60-61-45-36/37
RIDADR	UN 2811 6.1/PG 3
WGK Germany	1
RTECS-Nr.	NL2450000
F	8-13
TSCA	Yes
HS Code	2933 99 20
HazardClass	9
PackingGroup	III
Giftige Stoffe Daten	120-72-9(Hazardous Substances Data)
Toxizität	LD50 orally in rats: 1 g/kg (Smyth)

Gefahreninformationscode (GHS)

Indole Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R21/22:Gesundheitsschädlich bei Berührung mit der Haut und beim Verschlucken.
R37/38:Reizt die Atmungsorgane und die Haut.
R41:Gefahr ernster Augenschäden.
R50/53:Sehr giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
R36:Reizt die Augen.
R39/23/24/25:Giftig: ernste Gefahr irreversiblen Schadens durch Einatmen, Berührung mit der Haut und durch Verschlucken.
R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S60:Dieses Produkt und sein Behälter sind als gefährlicher Abfall zu entsorgen.
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
Aussehen Eigenschaften
C87N. Farbloser Feststoff mit charakteristischem Geruch.
Gefahren für Mensch und Umwelt
Gesundheitsschädlich beim Verschlucken und Berührung mit der Haut. Wird durch die Haut resorbiert.
LD₅₀ (oral, Ratte): 1000 mg/kg
Schutzmaßnahmen und Verhaltensregeln
Geeignete Schutzhandschuhe als kurzzeitiger Staubschutz.
Verhalten im Gefahrfall
Trocken aufnehmen. Der Entsorgung zuführen. Nachreinigen.
Kohlendioxid, Wasser, Pulver, Schaum.
Brennbar. Im Brandfall können nitrose Gase entstehen.
Erste Hilfe
Nach Hautkontakt: Mit reichlich Wasser abwaschen.
Nach Augenkontakt: Mit reichlich Wasser bei geöffnetem Lidspalt mindestens 10 Minuten ausspülen. Sofort Augenarzt hinzuziehen.
Nach Einatmen: Frischluft.
Nach Verschlucken: Reichlich Wasser trinken lassen. Erbrechen auslösen. Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminierte Kleidung entfernen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Gelöst in z.B. Aceton als halogenfreie, organische Lösemittelabfälle.
Beschreibung
Indole has an almost floral odor when highly purified. Otherwise, it exhibits the characteristic odor of feces. It is not very stable on exposure to light (turns red). Indole may be obtained from the 220 - 260°C boiling fraction of coal tar or by heating sodium phenylglycine-o-carboxylate with NaOH, saturating the aqueous solution of the melt with C 02, and finally reducing with sodium amalgam; can be prepared also by the reduction of indoxyl, indoxyl carboxylic acid, or indigo.
Chemische Eigenschaften
Indole has an unpleasant odor at high concentration, odor becomes floral at higher dilutions
Chemische Eigenschaften
white crystals with an unpleasant odour
Physikalische Eigenschaften
Colorless to yellow scales with an unpleasant odor. Turns red on exposure to light and air. Odor threshold of 0.14 ppm was reported by Buttery et al. (1988).
Occurrence
Reported occurring in several natural products as a complex compound that decomposes during enfleurage or steam distillation yielding free indole; reported found in the essential oil from flower of Jasminum grandiflorum, in neroli oil and in the oil extracted from flowers of bitter orange; also reported in the flowers of several plants: lemon, coffee, Hevea brasiliensis and Randia formosa in the oil extracted from flowers of Jasminum odoratissinium L. and in the oil of Narcissus jonquilla. Also reported found in apricot, mandarin orange peel oil, grapes, kohlrabi, French fried potato, crispbread, cheeses, butter, milk, milk powder, boiled egg, fish oil, chicken, beef, pork, beer, rum, Finnish whiskey, red and white wine, coffee, tea, soybean, mushrooms, cauliflower, figs, rice, licorice, buckwheat, malt, wort, elder flower, clary sage, shrimp, okra, crab, clam, squid and green maté
Verwenden
Can be used in perfumes and in the synthesis of tryptophan.
Verwenden
In highly dil solutions the odor is pleasant, hence indole has been used in perfumery.
Verwenden
Indole occurs in coal tar. It is used, underhigh dilution, in perfumery, and as an intermediatein organic synthesis.
Verwenden
Indole is a flavoring agent that is a white, flaky crystalline product. it has an unpleasant odor when concentrated and a flowery odor when diluted. it is soluble in most fixed oils and propylene glycol and insoluble in glycerin and mineral oil. it is obtained from decomposi- tion of a protein.
synthetische
Obtained from the 220 to 260°C boiling fraction of coal tar or by heating sodium phenyl-glycine-o-carboxylate with NaOH, saturating the aqueous solution of the melt with CO2 and finally reducing with sodium amalgam; can be prepared also by the reduction of indoxyl, indoxyl carboxylic acid or indigo.
Definition
indole: A yellow solid, C₈H₇N, m.p.52°C. Its molecules consist of a benzenering fused to a nitrogen-containingfive-membered ring. It occurs insome plants and in coal tar, and isproduced in faeces by bacterial action.It is used in making perfumes.Indole has the nitrogen atom positionednext to the fused benzenering. An isomer with the nitrogentwo atoms away from the fused ringis called isoindole.
Aroma threshold values
Detection: 140 ppb
Synthesis Reference(s)
The Journal of Organic Chemistry, 55, p. 580, 1990 DOI: 10.1021/jo00289a036
Chemical and Pharmaceutical Bulletin, 35, p. 1823, 1987 DOI: 10.1248/cpb.35.1823
Allgemeine Beschreibung
Indole is classified under the volatile flavor compounds (VFCs). It is known to play significant role in various biological functions such as anti-inflammatory, anticonvulsant, cardiovascular and antibacterial activities.
Hazard
A carcinogen.
Health Hazard
Low to moderate toxicity was observed inexperimental animals resulting from oral orsubcutaneous administration of indole. Theoral LD50 value in rats is 1000 mg/kg. It is ananimal carcinogen. It caused tumors in bloodand lungs in mice subjected to subcutaneousadministration.
Brandgefahr
Noncombustible solid.
Flammability and Explosibility
Not classified
Biochem/physiol Actions
Taste at 0.3-2 ppm
Source
Indole was detected in jasmine flowers (Jasminum officinale), licorice (Glycyrrhiza glabra), kohlrabi stems (Brassica oleracea var. gongylodes), and hyacinth flowers (Hyacinthus orientalis) at concentrations of 42 to 95, 2, 1.33, and 0.24 to 3.45 ppm, respectively. Indole also occurs in tea leaves, black locust flowers, corn leaves, petitgrain, and yellow elder (Duke, 1992).
A liquid swine manure sample collected from a waste storage basin contained indole at a concentration of 4.8 mg/L (Zahn et al., 1997).
Environmental Fate
Biological. In 9% anaerobic municipal sludge, indole degraded to 1,3-dihydro-2H-indol-2-one (oxindole), which degraded to methane and carbon dioxide (Berry et al., 1987). Heukelekian and Rand (1955) reported a 5-d BOD value of 1.70 g/g which is 65.4% of the ThOD value of 2.48 g/g.
Chemical/Physical. The aqueous chlorination of indole by hypochlorite/hypochlorous acid, chlorine dioxide, and chloramines produced oxindole, isatin, and possibly 3-chloroindole (Lin and Carlson, 1984).
Stoffwechselwegen
The indole is metabolized in a mineral salt medium inoculated with 9% anaerobically digested nitrate- reducing sewage sludge, resulting in the sequential occurrence of four structurally related compounds: oxindole, isatine, dioxindole, and anthranilic acid. Indole is metabolized by fungus via indoxyl (3-hydroxyindole), N-formylanthranilic acid, anthranilic acid, 2,3-dihydroxybenzoic acid, and catecol, which is further degraded by an ortho cleavage.
Stoffwechsel
Indole is oxidized to 3-hydroxyindole (indoxyl) which is conjugated with glucuronic and sulphuric acids before excretion. The sulphate conjugate seems to be the main product in rabbits and, even with relatively large doses of indole, the sulphate conjugation always exceeds that of glucuronic acid(Williams, 1959).
läuterung methode
It can be further purified by sublimation in a vacuum or by zone melting. The picrate forms orange crystals from EtOH and has m 175o. [Beilstein 20 II 196, 20 III/IV 3176, 20/7 V 5.]
Toxicity evaluation
Indole causes oxidative damage to membranes.

Indole Upstream-Materialien And Downstream Produkte

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