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2,5-Di-tert-pentylhydrochinon

2,5-Di-t-pentylhydroquinone

HCID 6610
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Grundinformationen

CAS
79-74-3
Standard-SMILES
CCC(C)(C)c1cc(O)c(C(C)(C)CC)cc1O
InChIKey
CZNRFEXEPBITDS-UHFFFAOYSA-N
Summenformel
C16H26O2
Durchschnittliche Molmasse
250,38 g/mol
Monoisotopische Masse
250,19328007

Namen und Bezeichner

Bevorzugter Name
2,5-Di-t-pentylhydroquinone
IUPAC
2,5-bis(2-methylbutan-2-yl)benzene-1,4-diol
Lokaler Name
2,5-Di-tert-pentylhydrochinon
Englischer Name
2,5-Di(tert-amyl)hydroquinone
Summenformel
C16H26O2
Molmasse
250.38

Namen und Synonyme

79-74-32,5-Di-tert-amylhydroquinone2,5-Di-tert-pentylbenzene-1,4-diol2,5-Di-tert-pentylhydroquinoneSantovar ADiamylhydroquinoneAntage DAHUSAF B-211,4-Benzenediol, 2,5-bis(1,1-dimethylpropyl)-2,5-DI(TERT-AMYL)HYDROQUINONE2,5-Di-t-amylhydroquinone2,5-Bis(1,1-dimethylpropyl)hydroquinone
Weitere Namen anzeigen
DAHkyhjdahqSantovarusafb-21santouarasantovaraantagedahSantouar A
Hydroquinone, 2,5-di-tert-pentyl-Hydroquinone, 2,5-di-t-pentyl-NSC 455Hydroquinone, 2,5-di-tert-amyl-2,5-DI-T-PENTYLHYDROQUINONE2,5-Di-tert-amylbenzene-1,4-diol2,5-Bis(1,1-dimethylpropyl)-1,4-benzenediolHSDB 5231

Datenbank-Bezeichner

CAS
79-74-3
PubChem CID
6610

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,6
Polarare Oberfläche (TPSA)
40,5 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
4
Schwere Atome
18
Formalladung
0
Komplexität
242

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Phenols
CosmeticsAntioxidant
Density1.05 @ 25 °C
Color/Form · 2 Einträge

CRYSTALS

BUFF POWDER

SolubilitySLIGHTLY SOL IN WATER; SOL IN ALCOHOL & BENZENE
Melting Point179.4-180.4 °C
Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical Description · 2 Einträge

Dry Powder

Beige solid; [HSDB]

Physikochemische Eigenschaften

Schmelzpunkt
179 °C · 179 °C
Siedepunkt

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 81 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: 1,4-Benzenediol, 2,5-bis(1,1-dimethylpropyl)-

1,4-Benzenediol, 2,5-bis(1,1-dimethylpropyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,4-Benzenediol, 2,5-bis(1,1-dimethylpropyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: 2,5-di-tert-pentylhydroquinone (EC: 201-222-2)

1,4-Benzenediol, 2,5-bis(1,1-dimethylpropyl)-: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 Eintrag

Reproductive effector; Causes liver injury (abnormal liver function tests) and weight loss in feeding studies; [RTECS] Emergency treatment: see Hydroquinone and Quinone. [HSDB] An irritant; May cause skin burns and damage to lungs; [MSDSonline]

Hazard Classes and Categories · 3 Einträge

Acute Tox. 4 (100%)

Specific target organ toxicity - Single exposure - Category 2 (systemic toxicity)

Skin sensitization - Category 1A

Sicherheit und Schutzausrüstung

Chemie und Industrie

Pharmakologische Informationen

Absorption, Distribution and ExcretionCMPD WAS FOUND IN TISSUES INCL NEUROLOGICAL TUMORS, ADULT & FETAL BRAIN. NO CONTAMINATION SOURCE WAS FOUND IN HOSPITAL; POSSIBLE SOURCE: ANTIOXIDANT PREPN IN RUBBER MFR.

Verwendung und Herstellung

Uses · 3 Einträge

Used as an antioxidant for uncured rubber and unsaturated resins and oils; in food packaging; as a polymerization inhibitor; and as a staining protector in rubber; [HSDB]

ANTIOXIDANT FOR UNCURED RUBBER & FOR UNSATURATED RESINS & OILS; FOOD PACKAGING; POLYMERIZATION INHIBITOR

AS STAINING PROTECTOR IN RUBBER

U.S. Production2023: <50,000 lb
Industry UsesAntioxidant
Methods of Manufacturing · 2 Einträge

ERICKSON, BRITISH PATENT 596,461 (1948 TO MATHIESON ALKALI WORKS).

Hydroquinone + isoamylene (Friedel-Crafts alkylation)

Use ClassificationCosmetics -> Antioxidant
General Manufacturing Information · 2 Einträge

Plastics Material and Resin Manufacturing

1,4-Benzenediol, 2,5-bis(1,1-dimethylpropyl)-: ACTIVE

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

2,5-Di-tert-amylbenzoquinoneSchwefelsure2-Methylbut-2-en1,4-Dihydroxybenzol

Zugehörige Reaktionen

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Reaktionsaufzeichnung erstellen

Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.

Notizen zur Verbindung

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Auf dieser SeiteGrundinformationenNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
DTXSID
DTXSID5044992
ChEMBL
CHEMBL594135
UNII
19O4J76TTK
EC Number
201-222-2
Nikkaji
J10.508B
353.51 °C · 353.51°C (rough estimate)
Dichte
0.9781 · 0.9781 (rough estimate)
Dampfdruck
0 Pa · 0Pa at 20℃
Brechungsindex
1.6 · 1.6000 (estimate)
pka
11.21 · 11.21±0.23(Predicted)
Aggregatzustand
powder to crystal
Farbe
White to Yellow to Orange
Wasserlöslichkeit
200 ng/L · 200ng/L at 20℃
Merck
14 · 14,3304
Kosmetik-Inhaltsstoffe Funktionen
ANTIOXIDANT
LogP
5.1 at · 5.1 at 25℃
CAS Datenbank
79 · 79-74-3(CAS DataBase Reference)
NIST chemische Informationen
1 · 1,4-Benzenediol, 2,5-bis(1,1-dimethylpropyl)-(79-74-3)
EPA chemische Informationen
1 · 1,4-Benzenediol, 2,5-bis(1,1-dimethylpropyl)- (79-74-3)
Disposal Methods · 1 Eintrag

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Toxikologische Informationen

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
TSCA Test Submissions · 5 Einträge

2,5-di-t-pentylhydroquino (CAS # 79-74-3) was evaluated for dermal sensitization. The Shelanski and Shelanski Repeated Insult Patch Test was used, the test substance was administered to more than 50 adults. The induction phase included 10 occluded applications of 0.2 ml of a 50% dispersion of test substance to the intact skin on the left side of the back. No adverse responses occurred in 21 subjects. In another 21 subjects, responses not greater than a Grade 1 occurred. In 5 subjects, responses not greater than a Grade 2 occurred. Indurated erythematous (Grade 4) occurred once in 6 subjects and twice in 1 subject. Five weeks after the induction phase, the challenge phase included application of the test substance to naive sites at the same concentration as the induction phase. No adverse responses occurred in 37 subjects. In 9 subjects, responses not greater than a Grade 1 occurred. In 4 subjects, responses not greater than a Grade 2 occurred. In 3 subjects, a Grade 4 was obtained after the second application of the challenge phase. The test substance was determined to have a weak to moderate skin-irritating propensity.

2,5-di-t-pentylhydroquino (CAS # 79-74-3) was evaluated for teratogenic toxicity. The test substance was administered orally in a corn oil vehicle to pregnant Sprague-Dawley rats (25/group) at dosage levels of 0, 20, 70, or 175 mg/kg/day on gestation days 6-15. All doses were administered at a constant volume of 5 mg/kg. Clinical signs at 70 mg/kg/day were slight maternal toxicity and substantial maternal toxicity at 175 mg/kg/day. Signs of toxicity included post-dosing salivation, increased incidence of reddish colored vaginal discharge at the 70 mg/kg/day level, and more frequent and severe toxicity, body weight loss and reduced food consumption at the 175 mg/kg/day level. Fetal toxicity at 175 mg/kg/day, included statistically significant body weight loss and litters with ossification variations, such as an increased incidence of skull anomalies, 7th cervical ribs, and #5 and/or #6 sternebrae were unossified. The no observable effect level (NOEL) for maternal toxicity was 20 mg/kg/day, and the NOEL for developmental toxicity was 70 mg/kg/day.

2,5-di-t-pentylhydroquino (CAS # 79-74-3) was evaluated for the potential to induce structural chromosomal aberrations in the hemopoietic cells of the rat bone marrow when administered by oral gavage. The test substance was administered in single oral doses to three groups of fasted young albino Sprague-Dawley rats (number and sex of rats was not reported) at a dosage of 1000 mg/kg of body weight. Treated rats were evaluated at intervals of 6, 18, and 30 hours. Approximately 2 hours before each sacrifice time, rats were administered colchicine at 4 mg/kg of body weight to arrest cells in metaphase. Both femurs were removed from sacrificed animals and metaphase slides were prepared for scoring of chromosome aberrations. All rats exhibited mild to severe toxic signs, including diarrhea, abnormal gait, and stance. In the 18 hour group, toxic signs included decreased body tone and inactivity. In the 30 hour group, toxic signs included yellow to brown wet pellage in the anal-genital region and decreased body tone. From the 18 hour harvest group 2 females died. From each animal, 50 metaphase cells were analyzed. There were no statistically significant increase in the incidence of aberrations or number of aberrant metaphases observed at any of the three sampling times, therefore, the test substance was classified as not clastogenic.

2,5-di-t-pentylhydroquino (CAS # 79-74-3) was evaluated for mutagenicity in the rat liver homogenate metabolic activation system (S9). The test substance was tested in an insoluble concentration in aqueous media (greater than 100 ug/ml). Increases in cytotoxicity were observed as the S9 levels increased from 2% to 10%. Maximum concentrations tested in mutagenicity assays were 150 ug/ml in the absence of S9 and 100 ug/ml in the presence of 1%, 2%, 5%, and 10% S9. The test substance was determined not to be a mutagen.

For more TSCA Test Submissions (Complete) data for 2,5-DI-T-PENTYLHYDROQUINONE (6 total), please visit the HSDB record page.

Human Toxicity ExcerptsChronic neurotoxic effects include vision disturbances. /From table; Quinones/
Non-Human Toxicity Excerpts · 4 Einträge

2,5-DITERTIARY AMYL HYDROQUINONE WAS NON-HEMOLYTIC IN NORMAL RAT ERYTHROCYTES.

AFTER POS MATING OF WALTER REED-CARWORTH FARMS RATS IN THEIR 1ST GESTATION, FEMALES WERE RANDOMLY DISTRIBUTED INTO EXPTL & CONTROL GROUPS, FORMER GIVEN 2,5-DI-TERT-AMYLHYDROQUINONE BY MOUTH OR INTO DIET & KILLED 21 DAYS AFTER MATING. DATA SUGGEST BENEFICIAL EFFECT ON RESORPTION RATE.

Acute neurotoxic effects reported in animals include convulsions; medullary paralysis. /From table; Quinones/

The effects of diethyl maleate on the cytotoxicity of phenyl-hydroquinone and other hydroquinones were studied in freshly isolated rat hepatocytes. Addition of phenyl hydroquinone (O.5 or 0.75 mM) to hepatocytes resulted in dose-dependent cell death accompanied by the abrupt depletion of both glutathione and protein thiols and the accumulation of phenyl-benzoquinone. Pretreatment with diethyl maleate (1.25 mM) which causes an abrupt depletion of cellular glutathione in hepatocytes delayed the onset of phenyl hydroquinone-induced cytotoxicity. The delay correlated with inhibition of phenyl benzoquinone formation. Among other hydroquinones (0.5 mM), tert-butyl-hydroquinone-induced cytotoxicity was decreased by diethyl maleate (1.25 mM), but diethyl maleate did not affect the cytotoxicity of 2,5-di(tert-butyl)-1,4-benzohydroquinone. Phenyl-hydroquinone -induced cytotoxicity correlated with the accumulation of phenyl-benzoquinone in the cell.

Sicherheitsdaten

wgk
3
tsca
TSCA listed
hs_code
2914.69.9000
RTECS-Nr.
MX6300000
Giftige Stoffe Daten
79-74-3(Hazardous Substances Data)

Nachgelagerte Produkte

2-Ethoxyphenol3,5-Di-tert-butylbrenzcatechin

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