Basic information
- CAS
491-70-3- Standard SMILES
O=c1cc(-c2ccc(O)c(O)c2)oc2cc(O)cc(O)c12- InChIKey
IQPNAANSBPBGFQ-UHFFFAOYSA-N- Molecular formula
- C15H10O6
- Average molar mass
- 286.24 g/mol
- Monoisotopic mass
- 286.04773803
Names & identifiers
- Preferred name
- Luteolin
- IUPAC
- 2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
- English name
- Luteolin
- Molecular formula
- C15H10O6
- Molecular weight
- 286.24
Names & synonyms
Show more names
Database identifiers
- CAS
491-70-3- PubChem CID
- 5280445
- DTXSID
DTXSID4074988- ChEMBL
CHEMBL151- ChEBI
CHEBI:15864- UNII
- KUX1ZNC9J2
- EC Number
- 207-741-0
- Nikkaji
- J1.554G
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 107 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 1
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 447
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 330 °C · ~330 °C(lit.)
- Boiling point
- 348.61 °C · 348.61°C (rough estimate)
- Density
- 1.2981 · 1.2981 (rough estimate)
- refractive index
- 1.4413 · 1.4413 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Methanol (Slightly, Heated)
- form
- powder
- pka
- 6.5 · 6.50±0.40(Predicted)
- color
- yellow
- Water Solubility
- Soluble in aqueous alkaline solutions (1.4 mg/ml), ethanol (~5 mg/ml), dimethyl sulfoxide (7 mg/ml), 1eq. Sodium hydroxide (5 mM), dimethylformamide (~20 mg/ml), water (1 mg/ml) at 25°C and methanol.
- Merck
- 14 · 14,5614
- BRN
- 292084 · 292084
- Major Application
- food and beverages
- Cosmetics Ingredients Functions
- SKIN CONDITIONING
- InChI
- 1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H
- InChIKey
- IQPNAANSBPBGFQ-UHFFFAOYSA-N
- SMILES
- Oc1cc(O)c2C(=O)C=C(Oc2c1)c3ccc(O)c(O)c3
- LogP
- 2.4 · 2.40
- CAS DataBase Reference
- 491 · 491-70-3(CAS DataBase Reference)
- EWG's Food Scores
- 4 · 4
- FDA UNII
- 1 ZNC9J2 · KUX1ZNC9J2
- NCI Drug Dictionary
- luteolin
- EPA Substance Registry System
- Luteolin (491-70-3)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36-36/37/39
- WGK Germany
- 3 · 3
- RTECS
- 9275210 · LK9275210
- HS Code
- 29329990 · 29329990
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 1.9% (1 of 54) of reports.
Warning
H315 (98.1%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (98.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (96.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 54 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 54 reports by companies.;There are 9 notifications provided by 53 of 54 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Safety data
- wgk
- 3
- rtecs
- LK9275210
- hs_code
- 29329990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36-36/37/39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Pharmacology
Applications
DescriptionLuteolin is a flavone derived from Honeysuckle(Lonicera japonica Thunb). Luteolin is widely distributed in nature. It can be isolated from a variety of natural herbs, vegetables, and fruits. At present, luteolin is found mainly in honeysuckle, chrysanthemum, Schizonepeta, Ajuga, artichokes, Scutellaria, and Callicarpa nudiflora natural herbs.[3] Dietary sources include celery, broccoli, green pepper, parsley, thyme, dandelion, perilla, chamomile tea, carrots, olive oil, peppermint, rosemary, navel oranges, and oregano. It can also be found in the seeds of the palm Aiphanes aculeata.Fig 2 Source of Luteolin[4]
HistoryAt present, luteolin does not have the application of the proprietary medicine, but as one of the main active ingredients of medicinal plants, there is a long history of application. In northern and southern dynasties, honeysuckle with sweet taste, nontoxic, can treat swelling, lose weight, and prolong life under long-term use. In Tang dynasty, honeysuckle was used for treatment of abdominal distension, hot toxic blood dysentery, and water dysentery. It was showed that the clinical application of honeysuckle had made significant progress. During the Song and Yuan dynasties, honeysuckle was widely used for the treatment of diseases such as sore and ulcer. To the Ming dynasty, there were many treatises about honeysuckle. For example, it is said in Compendium of Materia Medica: honeysuckle cure all rheumatism QI and all sorts of swollen poison, ulcer,scab, and heat dissipation detoxify. The prescription has also expanded its scope of application. Up to the Qing dynasty, the application of honeysuckle can not only inherit the theory of the predecessors but also put forward some original ideas and innovation in some respects. In recent years, through the in-depth study of pharmacological effects, it is found that luteolin has significant effects on antitumor, cardioprotection, neuroprotection,respiratory system, immune regulation, anti-inflammatory, spasmolysis, expectorant, anti-allergic, enzyme activities, antioxidant, diuretic, and other aspects.
UsesLuteolin has been used:to induce and elucidate the apoptotic pathway in renal cell carcinoma 786-O cellsas an additive in M9 minimal medium to induce nodF gene expressionas a reference standard to qualitatively and quantitatively analyse luteolin using reverse phase-high performance liquid chromatography with diode array detector (RP-HPLC-DAD)as a reaction supplement for β-galactosidase assayto elucidate the anti-inflammatory efficacy of luteolin in pseudorabies virus infected RAW264.7 cell line by measuring the anti-inflammatory mediators production and also cell viability and cytotoxicity assay
General DescriptionLuteolin is a naturally occurring flavone, readily present in vegetables. It may possess many biological properties like anti-tumor activity against condition of skin papilloma. Luteolin is one of the most potent flavanoid inhibitors of soybean and reticulocyte 15-lipoxygenases, with an IC50 of 0.6 μM. Luteolin has also been found to inhibit the release of TNFα from neutrophils, and to inhibit matrix metalloproteinases.
Upstream & downstream products
Downstream products
Suppliers100 total
Additional notes
DefinitionChEBI: Luteolin is a tetrahydroxyflavone in which the four hydroxy groups are located at positions 3', 4', 5 and 7. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an anti-inflammatory agent and an immune system modulator as well as being active against several cancers. It has a role as an EC 2.3.1.85 (fatty acid synthase) inhibitor, an antineoplastic agent, a vascular endothelial growth factor receptor antagonist, a plant metabolite, a nephroprotective agent, an angiogenesis inhibitor, a c-Jun N-terminal kinase inhibitor, an anti-inflammatory agent, an apoptosis inducer, a radical scavenger and an immunomodulator. It is a 3'-hydroxyflavonoid and a tetrahydroxyflavone. It is a conjugate acid of a luteolin-7-olate.
Related reactions
Compound notes
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