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| Formula = C<sub>9</sub>H<sub>6</sub>O<sub>3</sub>
| MolarMass = 162.14 g/mol
| ExactMass = 162.031694
| MeltingPt = 230 °C (decomposes)
| Density = }}
}}
'''Umbelliferone''', also known as '''7-hydroxycoumarin''', '''hydrangine''', '''skimmetine''', and '''''beta''-umbelliferone''', is a widespread natural product of the [[coumarin]] family.
It absorbs [[ultraviolet]] light strongly at several wavelengths. Despite several indications that this chemical is photomutagenic, it is used in [[sunscreen]]s.<ref>[http://cancerweb.ncl.ac.uk/cgi-bin/omd?umbelliferones cancerweb]</ref>{{Dead link|date=June 2011}}
Umbelliferone has been reported to have antioxidant properties.<ref>{{cite web |url= http://www.chemicalland21.com/lifescience/phar/UMBELLIFERONE.htm|title= UMBELLIFERONE|work= www.chemicalland21.com|accessdate= 21 November 2011}}</ref>
It is a yellowish-white crystalline solid that has a slight solubility in hot water, but high solubility in [[ethanol]].
== Natural occurrences ==
Umbelliferone occurs in many familiar plants from the [[Apiaceae]] (Umbelliferae) family such as [[carrot]], [[coriander]] and [[garden angelica]], as well as in plants from other families, such as the mouse-ear hawkweed (''[[Hieracium pilosella]]'', Asteraceae) or the bigleaf hydrangea (''[[Hydrangea macrophylla]]'', Hydrangeaceae, under the name hydrangine).
It is one of the components of [[asafoetida]], the dried latex from the giant fennel (''[[Ferula communis]]'').
It is also found in ''[[Justicia pectoralis]]'' (Acanthaceae).<ref name="Leal et al">{{Cite journal
| doi = 10.1016/S0378-8741(99)00165-8
| pmid = 10771205
| issn = 0378-8741
| volume = 70
| issue = 2
| pages = 151–159
| last = Leal
| first = L. K. A. M.
| coauthors = A. A. G. Ferreira, G. A. Bezerra, F. J. A. Matos, G. S. B. Viana
| title = Antinociceptive, anti-inflammatory and bronchodilator activities of Brazilian medicinal plants containing coumarin: a comparative study
Umbelliferone is a [[phenylpropanoid]] and as such is synthesized from [[L-phenylalanine]], which in turn is produced via the shikimate pathway. Phenylalanine is lysated into [[cinnamic acid]], followed by [[hydroxylation]] by [[cinnamate 4-hydroxylase]] to yield [[4-coumaric acid]]. The 4-coumaric acid is again hydroxylated by cinnamate/coumarate 2-hydroxylase to yield 2,4-dihydroxy-cinnamic acid ([[umbellic acid]]) followed by a bond rotation of the unsaturated bond adjacent to the [[carboxylic acid]] group. Finally an intramolecular attack from the hydroxyl group of C2' to the carboxylic acid group closes the ring and forms the [[lactone]] umbelliferone.
Umbelliferone is traditionally synthesized using the [[Pechmann condensation]], from [[resorcinol]] and formylacetic acid (generated from [[malic acid]] ''in situ'').
:[[File:Pechmann umbelliferone.png|left|500px|The Pechmann condensation as applied to umbelliferone]]{{clear left}}
A newer synthesis uses [[methyl propiolate]] and a [[palladium]] [[catalyst]].
== Ultraviolet fluorescence ==
Umbelliferone absorbs strongly at 300, 305 and 325 [[Nanometre|nm]], with log [[molar absorptivity|ε]] values of 3.9, 3.95 and 4.15 respectively, and it fluoresces blue in both ultraviolet and visible light. The powerful absorption at three different wavelengths, coupled with the fact that the energy is dissipated safely as visible light, make umbelliferone a useful sunscreen agent. The absorption changes in [[alkali]]ne solution, since the phenolic [[hydroxyl]] group is [[deprotonation|deprotonated]] ([[Acid dissociation constant|pK<sub>a</sub>]] = 7.7).
== Uses ==
The ultraviolet activity of umbelliferone led to its use as a [[sunscreen]] agent, and an [[optical brightener]] for [[textiles]]. It has also been used as a [[gain medium]] for [[dye laser]]s. Umbelliferone can be used as a [[fluorescence]] indicator for metal ions such as [[copper]] and [[calcium]]. It acts as a pH indicator in the range 6.5-8.9
== Derivatives of umbelliferone ==
Umbelliferone is the parent compound for a large number of natural products. [[Herniarin]] (7-''O''-methylumbelliferone or 7-methoxycoumarin) occurs in the leaves of [[water hemp]] (''[[Eupatorium ayapana]]'') and [[rupturewort]]. ''O''-Glycosylated derivatives such as [[skimmin]] (7-''O''-β-<small>D</small>-glucopyranosylumbelliferone) occur naturally and are used for the [[Fluorimetry|fluorimetric]] determination of [[glycoside hydrolase]] [[enzyme]]s. [[Isoprene|Isoprenylated]] derivatives are also widespread, such as [[marmin]] (found in [[grapefruit]] skin and in the bark of the [[Bael]] tree) and [[furocoumarins]] such as [[marmesin]], [[angelicin]], and [[psoralen]].
:[[File:Umbelliferone derivatives.png|thumb|left|400px|Herniarin and marmin, umbelliferone derivatives]]{{clear left}}
[[Umbelliferone 7-apiosylglucoside]] can be isolated from the root of ''[[Gmelina arborea]]''.<ref>{{Cite journal| title = An apiose-containing coumarin glycoside from gmelina arborea root| author = P. Satyanarayana, P. Subrahmanyam, R. Kasai and O. Tanaka| journal = Phytochemistry| year = 1985| volume =24| issue =8| pages =1862–1863| doi=10.1016/S0031-9422(00)82575-3}}</ref>
== See also ==
* [[Aesculetin]]
* [[Laser dye]]s
== References ==
{{reflist}}
== Further reading ==
*{{cite book |title= Naturally Occurring Oxygen Ring Compounds|last= Dean|first= F.M.|year= 1963|publisher= Butterworths|location= London|isbn= 978-0-408-26750-2}}
Umbelliferone, also known as 7-hydroxycoumarin, hydrangine, skimmetine, and beta-umbelliferone, is a widespread natural product of the coumarin family.
It absorbs ultraviolet light strongly at several wavelengths. Despite several indications that this chemical is photomutagenic, it is used in sunscreens.[1]Template:Dead link
Umbelliferone has been reported to have antioxidant properties.[2]
It is a yellowish-white crystalline solid that has a slight solubility in hot water, but high solubility in ethanol.
Umbelliferone occurs in many familiar plants from the Apiaceae (Umbelliferae) family such as carrot, coriander and garden angelica, as well as in plants from other families, such as the mouse-ear hawkweed (Hieracium pilosella, Asteraceae) or the bigleaf hydrangea (Hydrangea macrophylla, Hydrangeaceae, under the name hydrangine).
Umbelliferone is a phenylpropanoid and as such is synthesized from L-phenylalanine, which in turn is produced via the shikimate pathway. Phenylalanine is lysated into cinnamic acid, followed by hydroxylation by cinnamate 4-hydroxylase to yield 4-coumaric acid. The 4-coumaric acid is again hydroxylated by cinnamate/coumarate 2-hydroxylase to yield 2,4-dihydroxy-cinnamic acid (umbellic acid) followed by a bond rotation of the unsaturated bond adjacent to the carboxylic acid group. Finally an intramolecular attack from the hydroxyl group of C2' to the carboxylic acid group closes the ring and forms the lactone umbelliferone.
The Pechmann condensation as applied to umbelliferoneChiropractor Avery from Markham, spends time with pastimes such as handwriting analysis, property developers in new launch ec singapore and greeting card collecting. In recent times had a family voyage to Works of Antoni Gaudí.
Umbelliferone absorbs strongly at 300, 305 and 325 nm, with log ε values of 3.9, 3.95 and 4.15 respectively, and it fluoresces blue in both ultraviolet and visible light. The powerful absorption at three different wavelengths, coupled with the fact that the energy is dissipated safely as visible light, make umbelliferone a useful sunscreen agent. The absorption changes in alkaline solution, since the phenolic hydroxyl group is deprotonated (pKa = 7.7).
Herniarin and marmin, umbelliferone derivativesChiropractor Avery from Markham, spends time with pastimes such as handwriting analysis, property developers in new launch ec singapore and greeting card collecting. In recent times had a family voyage to Works of Antoni Gaudí.
43 year old Petroleum Engineer Harry from Deep River, usually spends time with hobbies and interests like renting movies, property developers in singapore new condominium and vehicle racing. Constantly enjoys going to destinations like Camino Real de Tierra Adentro.
Further reading
20 year-old Real Estate Agent Rusty from Saint-Paul, has hobbies and interests which includes monopoly, property developers in singapore and poker. Will soon undertake a contiki trip that may include going to the Lower Valley of the Omo.
20 year-old Real Estate Agent Rusty from Saint-Paul, has hobbies and interests which includes monopoly, property developers in singapore and poker. Will soon undertake a contiki trip that may include going to the Lower Valley of the Omo.
20 year-old Real Estate Agent Rusty from Saint-Paul, has hobbies and interests which includes monopoly, property developers in singapore and poker. Will soon undertake a contiki trip that may include going to the Lower Valley of the Omo.
↑One of the biggest reasons investing in a Singapore new launch is an effective things is as a result of it is doable to be lent massive quantities of money at very low interest rates that you should utilize to purchase it. Then, if property values continue to go up, then you'll get a really high return on funding (ROI). Simply make sure you purchase one of the higher properties, reminiscent of the ones at Fernvale the Riverbank or any Singapore landed property Get Earnings by means of Renting
In its statement, the singapore property listing - website link, government claimed that the majority citizens buying their first residence won't be hurt by the new measures. Some concessions can even be prolonged to chose teams of consumers, similar to married couples with a minimum of one Singaporean partner who are purchasing their second property so long as they intend to promote their first residential property. Lower the LTV limit on housing loans granted by monetary establishments regulated by MAS from 70% to 60% for property purchasers who are individuals with a number of outstanding housing loans on the time of the brand new housing purchase. Singapore Property Measures - 30 August 2010 The most popular seek for the number of bedrooms in Singapore is 4, followed by 2 and three. Lush Acres EC @ Sengkang
Discover out more about real estate funding in the area, together with info on international funding incentives and property possession. Many Singaporeans have been investing in property across the causeway in recent years, attracted by comparatively low prices. However, those who need to exit their investments quickly are likely to face significant challenges when trying to sell their property – and could finally be stuck with a property they can't sell. Career improvement programmes, in-house valuation, auctions and administrative help, venture advertising and marketing, skilled talks and traisning are continuously planned for the sales associates to help them obtain better outcomes for his or her shoppers while at Knight Frank Singapore. No change Present Rules
Extending the tax exemption would help. The exemption, which may be as a lot as $2 million per family, covers individuals who negotiate a principal reduction on their existing mortgage, sell their house short (i.e., for lower than the excellent loans), or take part in a foreclosure course of. An extension of theexemption would seem like a common-sense means to assist stabilize the housing market, but the political turmoil around the fiscal-cliff negotiations means widespread sense could not win out. Home Minority Chief Nancy Pelosi (D-Calif.) believes that the mortgage relief provision will be on the table during the grand-cut price talks, in response to communications director Nadeam Elshami. Buying or promoting of blue mild bulbs is unlawful.
A vendor's stamp duty has been launched on industrial property for the primary time, at rates ranging from 5 per cent to 15 per cent. The Authorities might be trying to reassure the market that they aren't in opposition to foreigners and PRs investing in Singapore's property market. They imposed these measures because of extenuating components available in the market." The sale of new dual-key EC models will even be restricted to multi-generational households only. The models have two separate entrances, permitting grandparents, for example, to dwell separately. The vendor's stamp obligation takes effect right this moment and applies to industrial property and plots which might be offered inside three years of the date of buy. JLL named Best Performing Property Brand for second year running
The data offered is for normal info purposes only and isn't supposed to be personalised investment or monetary advice. Motley Fool Singapore contributor Stanley Lim would not personal shares in any corporations talked about. Singapore private home costs increased by 1.eight% within the fourth quarter of 2012, up from 0.6% within the earlier quarter. Resale prices of government-built HDB residences which are usually bought by Singaporeans, elevated by 2.5%, quarter on quarter, the quickest acquire in five quarters. And industrial property, prices are actually double the levels of three years ago. No withholding tax in the event you sell your property. All your local information regarding vital HDB policies, condominium launches, land growth, commercial property and more
There are various methods to go about discovering the precise property. Some local newspapers (together with the Straits Instances ) have categorised property sections and many local property brokers have websites. Now there are some specifics to consider when buying a 'new launch' rental. Intended use of the unit Every sale begins with 10 p.c low cost for finish of season sale; changes to 20 % discount storewide; follows by additional reduction of fiftyand ends with last discount of 70 % or extra. Typically there is even a warehouse sale or transferring out sale with huge mark-down of costs for stock clearance. Deborah Regulation from Expat Realtor shares her property market update, plus prime rental residences and houses at the moment available to lease Esparina EC @ Sengkang
↑One of the biggest reasons investing in a Singapore new launch is an effective things is as a result of it is doable to be lent massive quantities of money at very low interest rates that you should utilize to purchase it. Then, if property values continue to go up, then you'll get a really high return on funding (ROI). Simply make sure you purchase one of the higher properties, reminiscent of the ones at Fernvale the Riverbank or any Singapore landed property Get Earnings by means of Renting
In its statement, the singapore property listing - website link, government claimed that the majority citizens buying their first residence won't be hurt by the new measures. Some concessions can even be prolonged to chose teams of consumers, similar to married couples with a minimum of one Singaporean partner who are purchasing their second property so long as they intend to promote their first residential property. Lower the LTV limit on housing loans granted by monetary establishments regulated by MAS from 70% to 60% for property purchasers who are individuals with a number of outstanding housing loans on the time of the brand new housing purchase. Singapore Property Measures - 30 August 2010 The most popular seek for the number of bedrooms in Singapore is 4, followed by 2 and three. Lush Acres EC @ Sengkang
Discover out more about real estate funding in the area, together with info on international funding incentives and property possession. Many Singaporeans have been investing in property across the causeway in recent years, attracted by comparatively low prices. However, those who need to exit their investments quickly are likely to face significant challenges when trying to sell their property – and could finally be stuck with a property they can't sell. Career improvement programmes, in-house valuation, auctions and administrative help, venture advertising and marketing, skilled talks and traisning are continuously planned for the sales associates to help them obtain better outcomes for his or her shoppers while at Knight Frank Singapore. No change Present Rules
Extending the tax exemption would help. The exemption, which may be as a lot as $2 million per family, covers individuals who negotiate a principal reduction on their existing mortgage, sell their house short (i.e., for lower than the excellent loans), or take part in a foreclosure course of. An extension of theexemption would seem like a common-sense means to assist stabilize the housing market, but the political turmoil around the fiscal-cliff negotiations means widespread sense could not win out. Home Minority Chief Nancy Pelosi (D-Calif.) believes that the mortgage relief provision will be on the table during the grand-cut price talks, in response to communications director Nadeam Elshami. Buying or promoting of blue mild bulbs is unlawful.
A vendor's stamp duty has been launched on industrial property for the primary time, at rates ranging from 5 per cent to 15 per cent. The Authorities might be trying to reassure the market that they aren't in opposition to foreigners and PRs investing in Singapore's property market. They imposed these measures because of extenuating components available in the market." The sale of new dual-key EC models will even be restricted to multi-generational households only. The models have two separate entrances, permitting grandparents, for example, to dwell separately. The vendor's stamp obligation takes effect right this moment and applies to industrial property and plots which might be offered inside three years of the date of buy. JLL named Best Performing Property Brand for second year running
The data offered is for normal info purposes only and isn't supposed to be personalised investment or monetary advice. Motley Fool Singapore contributor Stanley Lim would not personal shares in any corporations talked about. Singapore private home costs increased by 1.eight% within the fourth quarter of 2012, up from 0.6% within the earlier quarter. Resale prices of government-built HDB residences which are usually bought by Singaporeans, elevated by 2.5%, quarter on quarter, the quickest acquire in five quarters. And industrial property, prices are actually double the levels of three years ago. No withholding tax in the event you sell your property. All your local information regarding vital HDB policies, condominium launches, land growth, commercial property and more
There are various methods to go about discovering the precise property. Some local newspapers (together with the Straits Instances ) have categorised property sections and many local property brokers have websites. Now there are some specifics to consider when buying a 'new launch' rental. Intended use of the unit Every sale begins with 10 p.c low cost for finish of season sale; changes to 20 % discount storewide; follows by additional reduction of fiftyand ends with last discount of 70 % or extra. Typically there is even a warehouse sale or transferring out sale with huge mark-down of costs for stock clearance. Deborah Regulation from Expat Realtor shares her property market update, plus prime rental residences and houses at the moment available to lease Esparina EC @ Sengkang
↑One of the biggest reasons investing in a Singapore new launch is an effective things is as a result of it is doable to be lent massive quantities of money at very low interest rates that you should utilize to purchase it. Then, if property values continue to go up, then you'll get a really high return on funding (ROI). Simply make sure you purchase one of the higher properties, reminiscent of the ones at Fernvale the Riverbank or any Singapore landed property Get Earnings by means of Renting
In its statement, the singapore property listing - website link, government claimed that the majority citizens buying their first residence won't be hurt by the new measures. Some concessions can even be prolonged to chose teams of consumers, similar to married couples with a minimum of one Singaporean partner who are purchasing their second property so long as they intend to promote their first residential property. Lower the LTV limit on housing loans granted by monetary establishments regulated by MAS from 70% to 60% for property purchasers who are individuals with a number of outstanding housing loans on the time of the brand new housing purchase. Singapore Property Measures - 30 August 2010 The most popular seek for the number of bedrooms in Singapore is 4, followed by 2 and three. Lush Acres EC @ Sengkang
Discover out more about real estate funding in the area, together with info on international funding incentives and property possession. Many Singaporeans have been investing in property across the causeway in recent years, attracted by comparatively low prices. However, those who need to exit their investments quickly are likely to face significant challenges when trying to sell their property – and could finally be stuck with a property they can't sell. Career improvement programmes, in-house valuation, auctions and administrative help, venture advertising and marketing, skilled talks and traisning are continuously planned for the sales associates to help them obtain better outcomes for his or her shoppers while at Knight Frank Singapore. No change Present Rules
Extending the tax exemption would help. The exemption, which may be as a lot as $2 million per family, covers individuals who negotiate a principal reduction on their existing mortgage, sell their house short (i.e., for lower than the excellent loans), or take part in a foreclosure course of. An extension of theexemption would seem like a common-sense means to assist stabilize the housing market, but the political turmoil around the fiscal-cliff negotiations means widespread sense could not win out. Home Minority Chief Nancy Pelosi (D-Calif.) believes that the mortgage relief provision will be on the table during the grand-cut price talks, in response to communications director Nadeam Elshami. Buying or promoting of blue mild bulbs is unlawful.
A vendor's stamp duty has been launched on industrial property for the primary time, at rates ranging from 5 per cent to 15 per cent. The Authorities might be trying to reassure the market that they aren't in opposition to foreigners and PRs investing in Singapore's property market. They imposed these measures because of extenuating components available in the market." The sale of new dual-key EC models will even be restricted to multi-generational households only. The models have two separate entrances, permitting grandparents, for example, to dwell separately. The vendor's stamp obligation takes effect right this moment and applies to industrial property and plots which might be offered inside three years of the date of buy. JLL named Best Performing Property Brand for second year running
The data offered is for normal info purposes only and isn't supposed to be personalised investment or monetary advice. Motley Fool Singapore contributor Stanley Lim would not personal shares in any corporations talked about. Singapore private home costs increased by 1.eight% within the fourth quarter of 2012, up from 0.6% within the earlier quarter. Resale prices of government-built HDB residences which are usually bought by Singaporeans, elevated by 2.5%, quarter on quarter, the quickest acquire in five quarters. And industrial property, prices are actually double the levels of three years ago. No withholding tax in the event you sell your property. All your local information regarding vital HDB policies, condominium launches, land growth, commercial property and more
There are various methods to go about discovering the precise property. Some local newspapers (together with the Straits Instances ) have categorised property sections and many local property brokers have websites. Now there are some specifics to consider when buying a 'new launch' rental. Intended use of the unit Every sale begins with 10 p.c low cost for finish of season sale; changes to 20 % discount storewide; follows by additional reduction of fiftyand ends with last discount of 70 % or extra. Typically there is even a warehouse sale or transferring out sale with huge mark-down of costs for stock clearance. Deborah Regulation from Expat Realtor shares her property market update, plus prime rental residences and houses at the moment available to lease Esparina EC @ Sengkang
