| Identification | More | [Name]
Orcinol | [CAS]
504-15-4 | [Synonyms]
1,3-DIHYDROXY-5-METHYLBENZENE
2,6-DIMETHYLRESORCINOL
3,5-DIHYDROXYTOLUENE
5-METHYL-1,3-BENZENEDIOL
5-METHYLRESORCINOL
AKOS 92132
ORCINOL
TIMTEC-BB SBB006928
1,3-Benzenediol, 5-methyl-
3,5-Dihydroxytoluene,monohydra
3,5-Orcinol
3,5-Toluenediol
3-Benzenediol,5-methyl-1
3-Hydroxy-5-methylphenol
5-methyl-3-benzenediol
5-Methylresorcin
5-methyl-resorcino
Methylresorcinol
Orcin
orcinol,5-methylresorcinol | [EINECS(EC#)]
207-984-2 | [Molecular Formula]
C7H8O2 | [MDL Number]
MFCD00002291 | [Molecular Weight]
124.14 | [MOL File]
504-15-4.mol |
| Chemical Properties | Back Directory | [Appearance]
pink-grey to pink-brown cryst. powder or crystals | [Melting point ]
106-112 °C(lit.)
| [Boiling point ]
290 °C
| [density ]
1.2900 | [refractive index ]
1.4922 (estimate) | [Fp ]
159 °C
| [storage temp. ]
Store at <= 20°C. | [solubility ]
80g/l | [form ]
Crystalline Powder or Crystals | [pka]
9.56±0.10(Predicted) | [color ]
Pink-gray to pink-brown | [Sensitive ]
Air Sensitive | [Merck ]
14,6864 | [BRN ]
1071903 | [Stability:]
Hygroscopic | [InChIKey]
OIPPWFOQEKKFEE-UHFFFAOYSA-N | [LogP]
1.221 (est) | [CAS DataBase Reference]
504-15-4(CAS DataBase Reference) | [NIST Chemistry Reference]
3,5-Dihydroxytoluene(504-15-4) | [EPA Substance Registry System]
504-15-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R41:Risk of serious damage to eyes.
R37/38:Irritating to respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [RIDADR ]
2811 | [WGK Germany ]
3
| [RTECS ]
VH2100000
| [TSCA ]
Yes | [PackingGroup ]
III | [HS Code ]
29072900 | [Safety Profile]
Poison by
subcutaneous and intravenous routes.
Moderately toxic by ingestion and
intraperitoneal routes. Mildly toxic by skin
contact. When heated to decomposition it
emits acrid smoke and irritating fumes. | [Toxicity]
LD50 orally in Rabbit: > 2000 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
| Hazard Information | Back Directory | [Chemical Properties]
pink-grey to pink-brown cryst. powder or crystals | [Uses]
Orcinol can be used to synthesize:
- Orcinol-containing azacryptands for use in optical amplifiers and light-emitting devices.
- Ternary co-crystal with 4,4′-bipyridine.
- Low-density carbon aerogels in the presence of formaldehyde.
- PEG-orcinol coumarins with potent tyrosinase inhibitory activity.
| [Application]
Orcinol is found in many lichen species and It is used as an analytical reagent for pentoses, lignin, beet sugar, saccharoses, arabinose, and diastase. The orcinol assay was used for the direct assay of the number of glycolipids presents in the sample. The orcinol reagent was prepared by adding concentrated sulphuric acid, H2SO4 (98% w/w) and 0.19% orcinol (3,5-dihydroxytoluene) to distilled water. | [Definition]
ChEBI: A 5-alkylresorcinol in which the alkyl group is specified as methyl. | [Preparation]
Orcinol has been isolated from numerous lichen fungi (Robiquet, 1829) and can be synthesized by decarboxylation of orsellinic acid in Umbilicaria papulosa and Gliocladium roseum (Pettersson, 1965; Mosbach and Ehrensvard, 1966).
Orcinol was first prepared by dehydroacetic acid, a conversion that involved ring-opening of the pyrone to a triketone. This early experiment helped establish the rich condensation chemistry of polyketides. It can be obtained by fusing extract of aloes with potash, followed by acidification.
US3865884A: Preparation of orcinol | [Biological Activity]
Orcinol is a compound obtained from DHA which can mimic the biogenetic synthesis of phenolic compounds.
Orcinol is a polyketide synthase-derived phenol that has been found in F. graminearum and has diverse biological activities. It scavenges DPPH radicals (IC50 = 2.93 mM). Orcinol (2.5 and 5 mg/kg) increases the number of entries into and percentage of time spent in the open arms of the elevated plus maze in mice, indicating anxiolytic-like activity. It has also been used in the colorimetric detection of carbohydrates. | [target]
ERK | BDNF | [Purification Methods]
Crystallise orcinol from CHCl3/*benzene (2:3). See hydrate in previous entry. [Beilstein 6 H 882, 6 IV 5892.] |
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