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Umbelliferone information


Umbelliferone
Chemical structure of umbelliferone
Unbelliferone, or 7-hydroxycoumarin, is a yellowish white crystalline powder lacking the odor of coumarin, or any strong odor.
Names
Preferred IUPAC name
7-Hydroxy-2H-1-benzopyran-2-one
Other names
7-hydroxycoumarin, hydrangine, skimmetine, beta-umbelliferone
Identifiers
CAS Number
  • 93-35-6 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:27510 ☒N
ChEMBL
  • ChEMBL51628 checkY
ChemSpider
  • 4444774 checkY
ECHA InfoCard 100.002.038 Edit this at Wikidata
PubChem CID
  • 5281426
UNII
  • 60Z60NTL4G checkY
CompTox Dashboard (EPA)
  • DTXSID5052626 Edit this at Wikidata
InChI
  • InChI=1S/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H checkY
    Key: ORHBXUUXSCNDEV-UHFFFAOYSA-N checkY
  • InChI=1/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H
    Key: ORHBXUUXSCNDEV-UHFFFAOYAL
SMILES
  • c1cc(cc2c1ccc(=O)o2)O
Properties
Chemical formula
C9H6O3
Molar mass 162.14 g/mol
Appearance yellowish-white crystalline odorless powder
Melting point 230 °C (446 °F; 503 K) (decomposes)
Magnetic susceptibility (χ)
-88.22·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Umbelliferone, also known as 7-hydroxycoumarin, hydrangine, skimmetine, and beta-umbelliferone, is a natural product of the coumarin family.

It absorbs ultraviolet light strongly at several wavelengths. There are some indications that this chemical is antimutagenic,[1] it is used in sunscreens.[2] Umbelliferone has been reported to have antioxidant properties.[3][4]

It is a yellowish-white crystalline solid that has a slight solubility in hot water, but high solubility in ethanol.

  1. ^ Ohta T, Watanabe K, Moriya M, Shirasu Y, Kada T (1983). "Anti-mutagenic effects of coumarin and umbelliferone on mutagenesis induced by 4-nitroquinoline 1-oxide or UV irradiation in e. Coli". Mutation Research. 117 (1–2): 135–138. doi:10.1016/0165-1218(83)90160-x. PMID 6403855.
  2. ^ Du L (2008). "Rational design of a fluorescent hydrogen peroxide probe based on the umbelliferone fluorophore". Tetrahedron Letters. 49 (19): 3045–3048. doi:10.1016/j.tetlet.2008.03.063. PMC 2490821. PMID 19081820.
  3. ^ "UMBELLIFERONE". www.chemicalland21.com. Retrieved 21 November 2011.
  4. ^ Sim MO, Lee HI, Ham JR, Seo KI, Kim MJ, Lee MK (2015). "Anti-inflammatory and antioxidant effects of umbelliferone in chronic alcohol-fed rats". Nutr Res Pract. 9 (4): 364–369. doi:10.4162/nrp.2015.9.4.364. PMC 4523479. PMID 26244074.

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Umbelliferone

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Umbelliferone, also known as 7-hydroxycoumarin, hydrangine, skimmetine, and beta-umbelliferone, is a natural product of the coumarin family. It absorbs...

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Methoxsalen

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combination of the shikimate pathway, which produces umbelliferone, and the mevalonate pathway. Umbelliferone is a phenylpropanoid and as such is synthesized...

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Herniaria glabra

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North America and Europe. It contains herniarin, a methoxy analog of umbelliferone. Herniarin on www.liberherbarum.com Media related to Herniaria glabra...

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Hydrangea macrophylla

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roots of H. macrophylla. Hydrangine is another name for the coumarin umbelliferone, and may be responsible for the possible toxicity of the plant. Amacha...

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Psoralen

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addition of a fused furan ring, and may be considered as a derivative of umbelliferone. Psoralen occurs naturally in the seeds of Psoralea corylifolia, as...

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Phenylpropanoid

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which can be further modified into hydroxylated derivatives such as umbelliferone. Another use of p-coumaric acid via its thioester with coenzyme A, i...

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Hymecromone

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point of 194–195 °C. It is soluble in methanol and glacial acetic acid. Umbelliferone Coumarin Yang Y, Hamaguchi K (April 1980). "Hydrolysis of 4-methylumbelliferyl...

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Gmelina arborea

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of Gmelina arborea. The parent compounds are arboreol or gmelanone. Umbelliferone 7-apiosylglucoside can be isolated from the root. Five constituents...

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Dill

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transformed into the plant. Apiole and dillapiole Carvone Limonene Myristicin Umbelliferone Fresh and dried dill leaves (sometimes called "dill weed" or "dillweed"...

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Furanocoumarin

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coupling of dimethylallyl pyrophosphate (DMAPP) and 7-hydroxycoumarin (umbelliferone). Many furanocoumarin compounds are toxic. The phytochemicals enter...

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Dianthera pectoralis

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coumarin, which it produces in plenty, and which in combination with umbelliferone is responsible for many of its notable properties. It is also admixed...

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Ruta graveolens

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contains coumarins and limonoids. Cell cultures produce the coumarins umbelliferone, scopoletin, psoralen, xanthotoxin, isopimpinellin, rutamarin and rutacultin...

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Pechmann condensation

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performed under much milder conditions. This provides a useful route to umbelliferone derivatives: For coumarins unsubstituted at the 4-position, the method...

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Asafoetida

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The resin portion contains asaresinotannols A and B, ferulic acid, umbelliferone and four unidentified compounds. The volatile oil component is rich...

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Laser dye

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Polyphenyl ("polyphenyl 1") Rhodamine 6G Rhodamine B Rhodamine 123 Umbelliferone (also known as 7-hydroxycoumarin) Organic laser Solid state dye laser...

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Ayapana triplinervis

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alpha-terneol, ayapanin, ayapin, borneol, coumarin, sabinene, and umbelliferone, among many others.[citation needed] Phytochemical analysis of a methanolic...

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Passiflora

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compounds found in passion flowers are coumarins (e.g. scopoletin and umbelliferone), maltol, phytosterols (e.g. lutenin) and cyanogenic glycosides (e.g...

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Chicory

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lactucopicrin. Other components are aesculetin, aesculin, cichoriin, umbelliferone, scopoletin, 6,7-dihydrocoumarin, and further sesquiterpene lactones...

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Bergamottin

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which is formed via the alkylation of the umbelliferone (2) compound. The alkylation of the umbelliferone is initiated with the use of dimethylallyl...

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Galbanum

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gum; and a very small quantity of the colorless crystalline substance umbelliferone. It also contains α-pinene, β-pinene, limonene, cadinene, 3-carene,...

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Coumarin

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of Justicia pectoralis Jacq. and its main constituents: coumarin and umbelliferone". Phytotherapy Research. 11 (3): 211–215. doi:10...

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Angelicin

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lactonizes to yield umbeliferone. Subsequently, umbelliferone 6-prenyltransferase (PT) couples umbelliferone with prenyl diphosphate to give osthenol and...

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Herniarin

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considered a methoxy derivative of coumarin or a methyl derivative of umbelliferone. Herniarin is found in Herniaria glabra, Ayapana triplinervis and in...

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Optical brightener

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2′-stilbenedisulfonic acid. Older, non-commercial fluorescent compounds include umbelliferone, which absorbs in the UV portion of the spectrum and re-emit it in the...

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Glossary of chemical formulae

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4-bromoisoquinoline 1532-97-4 C9H6N2 5-cyanoindole 15861-24-2 C9H6O3 umbelliferone 93-35-6 C9H6OS thiochromone 491-39-4 C9H7NO 8-hydroxyquinoline 148-24-3...

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Pilosella officinarum

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through stone as easily as through wood. The mouse-ear hawkweed contains umbelliferone, a compound similar to coumarin. The plant produces triterpenoids, mainly...

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Scopolia japonica

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tribe Hyoscyameae of the nightshade family Solanaceae. The coumarins umbelliferone and scopoletin have been isolated from the roots of Scopolia japonica...

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Umbellic acid

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isomer of caffeic acid. It is a precursor in the umbelliferone biosynthesis pathway. Umbelliferone is a phenylpropanoid and as such is synthesized from...

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Imperatorin

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younghusbandii, and Zanthoxylum americanum mill. It is biosynthesized from umbelliferone, a coumarin derivative. The procedure for the isolation of imperatorin...

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Scopolia

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cuscohygrine, hyoscyamine, and atroscine. The coumarin phenylpropanoids umbelliferone and scopoletin have been isolated from the roots of Scopolia japonica...

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