Basic information
- Standard SMILES
Oc1cc(O)cc(O)c1- InChIKey
QCDYQQDYXPDABM-UHFFFAOYSA-N- Molecular formula
- C6H6O3
- Average molar mass
- 126.11 g/mol
- Monoisotopic mass
- 126.03169405
Overview
Phloroglucinol is a benzenetriol with hydroxy groups at position 1, 3 and 5. It has a role as an algal metabolite. It is a phenolic donor and a benzenetriol.
Names & identifiers
- Preferred name
- Phloroglucinol
- IUPAC
- benzene-1,3,5-triol
- English name
- Phloroglucinol
- Molecular formula
- C6H6O3
- Molecular weight
- 126.11
Names & synonyms
phloroglucinol108-73-6Benzene-1,3,5-triol1,3,5-benzenetriol1,3,5-trihydroxybenzenePhloroglucinPhloroglucineSpasfon-LyocDilospan Ssym-Trihydroxybenzenes-TrihydroxybenzeneBenzene, trihydroxy
Show more names
3,5-DIHYDROXYPHENOLAnhydrous PhloroglucinolNero
FloroglucinFloroglucinolDHD7FFG6YSBenezene-1,3,5-triolNSC-1572DTXSID9048354CHEBI:16204RefChem:6129
Database identifiers
- CAS
108-73-6- PubChem CID
- 359
- DTXSID
DTXSID9048354- ChEMBL
CHEMBL473159- ChEBI
CHEBI:16204- UNII
- DHD7FFG6YS
- EC Number
- 203-611-2
- Nikkaji
- J2.866E
Properties
Computed structural properties
- XLogP
- 0.2
- Topological polar surface area
- 60.7 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 63.3
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Phenols
DrugsPharmaceuticals -> Listed in ZINC15
Cosmetics
Cosmetic ingredients (Phloroglucinol) -> CIR (Cosmetic Ingredient Review)
Hair dyeing
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP
0.16
0.16
Solubility10.6 mg/mL at 20 °C
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point218.5 °C
Vapor Pressure0.00016 [mmHg]
Physical Description
White solid; Discolored by light; [Merck Index] White or cream colored powder; [MSDSonline] Crystallizes in anhydrous or dihydrate form; Sweet tasting crystals; [Ullmann]
Solid
Collision Cross Section121.6 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID3046586]
Physicochemical properties
- Melting point
- 215 · 215-220 °C
- Boiling point
- 194.21 °C · 194.21°C (rough estimate)
- Density
- 0.801 g/mL · 0.801 g/mL at 20 °C
- bulk density
- 560 kg/m3 · 560kg/m3
- vapor pressure
- 0.001 Pa · 0.001Pa at 25℃
- refractive index
- 20 · n20/D 1.365
- Flash point
- 14 °C · 14 °C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- Soluble in diethyl ether, ethanol and pyridine.
- form
- Crystalline Powder
- pka
- 1 · pK1:8.45(0);pK2:8.88(-1) (25°C)
- color
- White to light beige
- Water Solubility
- 11.17 g/L · 11.17g/L(room temperature)
- Sensitive
- Light Sensitive & Hygroscopic
- Merck
- 14 · 14,7328
- BRN
- 1341907 · 1341907
- Cosmetics Ingredients Functions
- HAIR DYEING
- InChI
- 1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H
- InChIKey
- QCDYQQDYXPDABM-UHFFFAOYSA-N
- SMILES
- Oc1cc(O)cc(O)c1
- LogP
- 0.55 at · 0.55 at 25℃
- CAS DataBase Reference
- 108 · 108-73-6(CAS DataBase Reference)
- EWG's Food Scores
- 3 · 3-6
- FDA UNII
- 7 FFG6YS · DHD7FFG6YS
- ATC code
- 3 AX12 · A03AX12
- NIST Chemistry Reference
- 1 · 1,3,5-Benzenetriol(108-73-6)
- EPA Substance Registry System
- 1 · 1,3,5-Benzenetriol (108-73-6)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 11 · SE.11
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 303 · H303-H315-H319-H335
- Precautionary statements
- 501 · P501-P261-P271-P264-P280-P302+P352-P312-P337+P313-P305+P351+P338-P362+P364-P332+P313-P304+P340+P312-P403+P233-P405
- target organs
- Respiratory system
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- F,Xi
- Risk Statements
- 11 · 11-36/37/38-34-43
- Safety Statements
- 7 · 7-16-24/25-45-36/37/39-26-36/37-37/39
- RIDADR
- 1170 · UN 1170 3/PG 2
- WGK Germany
- 2 · 2
- RTECS
- 1050000 · SY1050000
- TSCA
- TSCA listed
- HS Code
- 29072900 · 29072900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3
- Toxicity
- 50 in · LD50 in mice, rats (g/kg): 4.7, 4.0 i.g. (Cahen)
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 1.9% (2 of 108) of reports.
Warning
H315 (81.5%): Causes skin irritation [Warning Skin corrosion/irritation]
P203, P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 108 reports by companies from 23 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 1,3,5-Benzenetriol
Status: Active Update: 25-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/23677
Phloroglucinol: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 1,3,5-Benzenetriol: Environment tier I assessment
Hazards SummaryA skin and eye irritant; [eChemPortal: ERMA] An irritant; [MSDSonline] Oral LD50 (mouse) = 4550 mg/kg; [Ullmann]
Hazard Classes and CategoriesSkin Irrit. 2 (81.5%)
Toxicology
Toxicity Summary
On the basis of the available data, the CIR Panel cannot conclude that Phloroglucinol is safe for use in cosmetic products until the appropriate safety data have been obtained and evaluated.
Ingredients for which the data are insufficient and their use in cosmetics is not supported
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Phloroglucinol
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- SY1050000
- ridadr
- UN 1170 3/PG 2
- hs_code
- 29072900
- Toxicity
- LD50 in mice, rats (g/kg): 4.7, 4.0 i.g. (Cahen)
- risk_code
- 11-36/37/38-34-43
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- F,Xi
- safety_code
- 7-16-24/25-45-36/37/39-26-36/37-37/39
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H303-H315-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3
- Precautionary statements
- P501-P261-P271-P264-P280-P302+P352-P312-P337+P313-P305+P351+P338-P362+P364-P332+P313-P304+P340+P312-P403+P233-P405
Chemistry & industry
Pharmacology
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
Metabolism/MetabolitesPhloroglucinol is a known human metabolite of Epicatechin and 2-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one.
MeSH Pharmacological Classification
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)
Uses & manufacturing
Uses
CIR ingredient: Phloroglucinol
Used to decalcify bones, to make pharmaceuticals and dyes, to preserve cut flowers, and to dye and print textiles; [Hawley] Used in diazo-type printing, cosmetics (antioxidant), hair colorants, chemical reagents, cloud seeding, tree and shrub rooting, and pharmaceuticals (antispasmodic); [Merck Index] Isolated from bark of fruit trees in 1855; [Ullmann]
Textiles (Printing, Dyeing, or Finishing) [Category: Industry]
Use ClassificationCosmetics -> Hair dyeing
General Manufacturing Information1,3,5-Benzenetriol: ACTIVE
Applications
UsesPhloroglucinol can be used in verifications of antimony, arsenic, cerium, chromate, chromium, gold, iron, mercury, nitrites, osmium, palladium, tin, vanadium, vanillin and lignin, and measurement of furfural, pentose, pentosan, methanol, chloral hydrate, turpentine, Lignified cell tissues, free acid in gastric juice (HCl) and decalcified bone specimens. Besides it can also be used as biological reagent dyes.
DescriptionPhloroglucinol is a naturally occurring phenol that exhibits diverse biological activities. Phloroglucinol protects V79-4 Chinese hamster lung fibroblast cells from oxidative stress and inhibits lipid peroxidation by scavenging reactive oxygen species (ROS). It induces apoptosis in HT-29 human colon cancer cells and inhibits metastasis of BT549 and MDA-MB-231 human breast cancer cells. Phloroglucinol protects primary neurons from β-amyloid-induced dendritic spine loss in vitro and shortens the latency to find the platform in a Morris water maze test in an Alzheimer’s disease (AD) mouse model. Phloroglucinol has been used to stain histological plant sections and in the synthesis of numerous natural products. Phloroglucinol slows the frequency and decreases the amplitude of contraction in isolated rabbit and rat intestine at a concentration of 100 and 1 μM, respectively. Formulations containing phloroglucinol have been used as antispasmodics.
UsesPhloroglucinol is mainly used as a coupling agent in printing. It is an active component of Tollen's reagent and Gunzburg reagent used to test pentoses and hydrochloric acid in gastric juice respectively. In analytical chemistry, it is used to study condensed tannins by means of depolymerization. It is also involved in the synthesis of 2,4,6-triamino-1,3,5- trinitrobenzene, trinitrophloroglucinol and pharmaceuticals like flopropione.
UsesPhloroglucinol (1,3,5-trihydroxybenzene) is the core structure of a large family of substituted phenolics with broad, albeit weak, biological activity. Phloroglucinol is a useful metabolite for HPLC/DAD and bioassay dereplication.diagnostic aid growth hormone releasing factor. Antispasmodic.
General DescriptionPhloroglucinol is a trihydroxybenzene with antithrombotic, profibrinolytic, antimicrobial, antimalarial, cancer chemopreventive, anti-HIV and anti-leishmanial activities. Phloroglucinol (PG) is a biosynthetic precursor of the 2,4-diacetylphloroglucinol (DAPG) an antibiotic against soil-borne diseases. Phloroglucinol is a useful intermediate because it is polyfunctional.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
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Additional notes
DefinitionChEBI: Phloroglucinol is a benzenetriol with hydroxy groups at position 1, 3 and 5. It has a role as an algal metabolite.
Related reactions
99 records
Linked notes
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