| Revision as of 12:57, 4 February 2012 editThe chemistds (talk | contribs)Extended confirmed users5,761 edits added PubchemID, CSID, (Std)InChI & (Std)InChIKey← Previous edit |
Latest revision as of 17:37, 11 September 2023 edit undoSmokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,208 edits no reason to repeat data in box |
| (24 intermediate revisions by 13 users not shown) |
| Line 1: |
Line 1: |
|
{{Chembox |
|
{{Chembox |
|
|
| Watchedfields = changed |
|
|
| verifiedrevid = 474948689 |
|
| ImageFile = Rosefuran-2D-skeletal.png |
|
| ImageFile = Rosefuran-2D-skeletal.png |
|
| ImageSize = 250px |
|
| ImageSize = 250px |
|
| IUPACName = 3-Methyl-2-(3-methyl-2-buten-1-yl)furan |
|
| PIN = 3-Methyl-2-(3-methylbut-2-en-1-yl)furan |
|
| OtherNames = 3-methyl-2-prenylfuran; 2-(3-Methyl-2-butenyl)-3-methylfuran |
|
| OtherNames = 3-methyl-2-prenylfuran; 2-(3-Methyl-2-butenyl)-3-methylfuran |
|
| Section1 = {{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
|
| CASNo_Ref = {{cascite|correct|??}} |
|
| CASNo = 15186-51-3 |
|
|
| PubChem = 84825 |
|
| CASNo = 15186-51-3 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
| ⚫ |
| ChemSpiderID = 76521 |
|
|
|
| UNII = PNC9VDU98G |
| ⚫ |
| SMILES = o1c(c(cc1)C)C\C=C(/C)C |
|
|
|
| PubChem = 84825 |
| ⚫ |
| InChI = 1/C10H14O/c1-8(2)4-5-10-9(3)6-7-11-10/h4,6-7H,5H2,1-3H3 |
|
|
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ⚫ |
| InChIKey = UTSGPHXOHJSDBC-UHFFFAOYAR |
|
|
⚫ |
| ChemSpiderID = 76521 |
| ⚫ |
| StdInChI = 1S/C10H14O/c1-8(2)4-5-10-9(3)6-7-11-10/h4,6-7H,5H2,1-3H3 |
|
|
⚫ |
| SMILES = o1c(c(cc1)C)C\C=C(/C)C |
| ⚫ |
| StdInChIKey = UTSGPHXOHJSDBC-UHFFFAOYSA-N |
|
|
⚫ |
| InChI = 1/C10H14O/c1-8(2)4-5-10-9(3)6-7-11-10/h4,6-7H,5H2,1-3H3 |
|
⚫ |
| InChIKey = UTSGPHXOHJSDBC-UHFFFAOYAR |
|
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
⚫ |
| StdInChI = 1S/C10H14O/c1-8(2)4-5-10-9(3)6-7-11-10/h4,6-7H,5H2,1-3H3 |
|
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
⚫ |
| StdInChIKey = UTSGPHXOHJSDBC-UHFFFAOYSA-N |
|
}} |
|
}} |
|
| Section2 = {{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| C = 10 | H = 14 | O = 1 |
|
| C=10 | H=14 | O=1 |
|
| Appearance = colorless liquid |
|
| Appearance = colorless liquid |
|
| Density = 0.9089 @30 °C |
|
| Density = 0.9089 @30 °C |
|
| MeltingPt = |
|
| MeltingPt = |
|
| BoilingPt = 103-104 °C @50 mm Hg |
|
| BoilingPtC = 103 to 104 |
|
|
| BoilingPt_notes = at 50 mmHg |
|
| Solubility = |
|
| Solubility = |
| ⚫ |
}} |
|
| ⚫ |
| Section3 = {{Chembox Hazards |
|
| ⚫ |
| MainHazards = |
|
| ⚫ |
| FlashPt = 144.00 °F |
|
|
| Autoignition = |
|
|
}} |
|
}} |
|
⚫ |
|Section3={{Chembox Hazards |
|
⚫ |
| MainHazards = |
|
⚫ |
| FlashPtF = 144.00 |
|
|
| AutoignitionPtC = |
|
⚫ |
}} |
|
}} |
|
}} |
|
'''Rosefuran''' (3-methyl-2-prenylfuran) is a liquid boiling at 103-104 °C (at 50 mm Hg), with a density of 0.9089 g/cm3 (at 30 °C), less than that of water.<ref>{{cite journal | author = B. Sanjiva Rao | title = The occurrence of furan derivatives in volatile oils. III. β-Clausenan and γ-clausenan | journal = Proceedings - Indian Academy of Sciences, Section A | volume = V3A | pages = 31-37 | year = 1936 |last2 = Subramaniam | first2 = K. S. | issue = 4}}</ref> It is an aroma chemical which is a minor constituent of the aroma of the rose (Rosa damascene). Rosefuran is a 2,3-disubstituted furan (3-methyl-2-(3-methyl-2-buten-1-yl)furan). It has an odor threshold of 200 ppb and constitutes 0.16% of Bulgarian rose oil.<ref>{{cite journal | author = Gunther Ohloff | title = Importance of minor components in flavors and fragrances | journal = Perfumer & Flavorist | volume = 3 | pages = 11-22 | year = 1978 | issue = 1}}</ref> Rosefuran has been established as a female sex pheromone of an acarid mite, Caloglyphus sp. Concentrations of less than 100 ng of synthetic rosefuran caused sexual excitation in males of the species.<ref>{{cite journal | author = Naoki Mori | title = Rosefuran: the sex pheromone of an acarid mite, Caloglyphus sp. | journal = Journal of Chemical Ecology | volume = 24 | pages = 1771-1779| year = 1998 |last2 = Kuwahara | first2 = Yasumasa | last3 = Kurosa | first3 = Kazuyoshi | issue = 11}}</ref> |
|
'''Rosefuran''' (3-methyl-2-prenylfuran) is an ], classified as a ].<ref>{{cite journal | author = B. Sanjiva Rao | title = The occurrence of furan derivatives in volatile oils. III. β-Clausenan and γ-clausenan | journal = Proceedings of the Indian Academy of Sciences, Section A | volume = V3A | pages = 31–37 | year = 1936 |last2 = Subramaniam | first2 = K. S. | issue = 4}}</ref> It is a minor constituent of the aroma of the rose (Rosa damascene). Rosefuran is a 2,3-disubstituted furan (3-methyl-2-(3-methyl-2-buten-1-yl)furan). It has an odor threshold of 200 ppb and constitutes 0.16% of Bulgarian rose oil.<ref>{{cite journal | author = Gunther Ohloff | title = Importance of minor components in flavors and fragrances | journal = Perfumer & Flavorist | volume = 3 | pages = 11–22 | year = 1978 | issue = 1}}</ref> Rosefuran has been established as a female sex pheromone of an acarid mite, Caloglyphus sp. Concentrations of less than 100 ng of synthetic rosefuran caused sexual excitation in males of the species.<ref>{{cite journal | author = Naoki Mori | title = Rosefuran: the sex pheromone of an acarid mite, Caloglyphus sp. | journal = Journal of Chemical Ecology | volume = 24 | pages = 1771–1779| year = 1998 |last2 = Kuwahara | first2 = Yasumasa | last3 = Kurosa | first3 = Kazuyoshi | issue = 11| doi = 10.1023/a:1022399331397 }}</ref> |
|
|
|
|
|
== Synthesis == |
|
== Synthesis == |
|
Rosefuran has been synthesized in many steps from common starting materials starting with prenyl chloride (3-methyl-but-2-en-1-yl chloride).<ref>{{cite journal | author = Seiichi Takano | title = Syntheses of perillene and rosefuran from common starting materials | journal = Chemistry Letters | volume = 7 | pages = 1261-1262 | year = 1984 |last2 = Morimoto | first2 = Masamichi | last3 = Satoh | first3 = Shigeki}}</ref> Rosefuran has also been synthesized via cyclization of suitable acyclic precursors, such as, 5-oxogeraniol and 5-hydroxycitral (4-hydoxy-3,7-dimethyl-(E)-2,6-octadienol).<ref>{{cite journal | author = Ryozo Iriye | title = The formation of alkylfurans from (E)-4-hydroxy-2-alkenals and (E)-4-oxo-2-alkenols, and a synthesis of rosefuran | journal = Agricultural and Biological Chemistry | volume = 54 | pages = 1841-1843| year = 1990 |last2 = Uno | first2 = Tsuyoshi | last3 = Ohwa | first3 = Ikuo | issue = 7}}</ref> Rosefuran has also been prepared via palladium catalyzed cross coupling of the methyl ester of 4-bromo-5-methyl-2-furancarboxylic acid followed by decarboxylation. <ref>{{cite journal | author = T. Bach | title = Regioselective Pd(0)-catalyzed coupling reactions on methyl 2,3-dibromofuran-5-carboxylate as a facile entry into 2,3,5-tri- and 2,3-disubstituted furans | journal = Synlett | volume = 11 | pages = 1185-1186| year = 1998 |last2 = Krueger| first2 = L.}}</ref> |
|
Rosefuran was synthesized in 1968 by ] via the ] bis(3-methyl-2-furyl)mercury.<ref>{{cite journal | first = George |last= Büchi| title = Synthesis of rosefuran and dehydroelsholtzione| journal = Journal of Organic Chemistry| volume = 33 |issue= 3 | pages =1227–9| year = 1968| last2 = Kovats| first2 = Erwin|last3 = Enggist| first3 = P.| last4 = Uhde| first4 = G . |doi=10.1021/jo01267a062}}</ref> Rosefuran has been synthesized in many steps from common starting materials starting with prenyl chloride (3-methyl-but-2-en-1-yl chloride).<ref>{{cite journal | author = Seiichi Takano | title = Syntheses of perillene and rosefuran from common starting materials | journal = Chemistry Letters | volume = 7 | pages = 1261–1262 | year = 1984 |last2 = Morimoto | first2 = Masamichi | last3 = Satoh | first3 = Shigeki | doi=10.1246/cl.1984.1261| doi-access = }}</ref> Rosefuran has also been synthesized via cyclization of suitable acyclic precursors, such as, 5-oxogeraniol and 5-hydroxycitral (4-hydoxy-3,7-dimethyl-(E)-2,6-octadienol).<ref>{{cite journal | author = Ryozo Iriye | title = The formation of alkylfurans from (E)-4-hydroxy-2-alkenals and (E)-4-oxo-2-alkenols, and a synthesis of rosefuran | journal = Agricultural and Biological Chemistry | volume = 54 | pages = 1841–1843| year = 1990 |last2 = Uno | first2 = Tsuyoshi | last3 = Ohwa | first3 = Ikuo | issue = 7 | doi=10.1271/bbb1961.54.1841| doi-access = free }}</ref> Rosefuran has also been prepared via palladium catalyzed cross coupling of the methyl ester of 4-bromo-5-methyl-2-furancarboxylic acid followed by decarboxylation.<ref>{{cite journal | author = T. Bach | title = Regioselective Pd(0)-catalyzed coupling reactions on methyl 2,3-dibromofuran-5-carboxylate as a facile entry into 2,3,5-tri- and 2,3-disubstituted furans | journal = Synlett | volume = 11 | pages = 1185–1186| year = 1998 |last2 = Krueger| first2 = L. | doi=10.1055/s-1998-1911}}</ref> |
|
|
|
|
|
Alternatively, rosefuran has been prepared from other furan derivatives. Thus, ] of 3-methyl-2-furanacetaldehyde with triphenylphosphonium isopropylide gave rosefuran in 67% yield. The aldehyde was obtained via ] of 3-(vinyloxymethyl)furan.<ref>{{cite journal | author = O. P. Vig | title = Terpenoids. LXXXV. Claisen rearrangement involving the furan ring system. Synthesis of rosefuran and sesquirosefuran | journal = Journal of the Indian Chemical Society | volume = 51 | pages = 900-902| year = 1974 |last2 = Vig | first2 = A. K | last3 = Handa | first3 = V. K. | issue = 10}}</ref> Similarly, the readily available ] was reacted with 3,3-dimethylallyl bromide and ] in THF solution, followed by reaction at with methyl iodide and ] in THF, yielding ].<ref>{{cite journal | author = Peter Weyerstahl | title = Structure-odor correlation. Part XXI. Olfactory properties and convenient synthesis of furans and thiophenes related to rosefuran and perillene and their isomers | journal = Liebigs Annalen | volume = 6 | pages = 1849-1853| year = 1995 |last2 = Schenk | first2 = Anja | last3 = Marschall | first3 = Helga | issue = 10}}</ref> |
|
Alternatively, rosefuran has been prepared from other furan derivatives. Thus, ] of 3-methyl-2-furanacetaldehyde with triphenylphosphonium isopropylide gave rosefuran in 67% yield. The aldehyde was obtained via ] of 3-(vinyloxymethyl)furan.<ref>{{cite journal | author = O. P. Vig | title = Terpenoids. LXXXV. Claisen rearrangement involving the furan ring system. Synthesis of rosefuran and sesquirosefuran | journal = Journal of the Indian Chemical Society | volume = 51 | pages = 900–902| year = 1974 |last2 = Vig | first2 = A. K | last3 = Handa | first3 = V. K. | issue = 10}}</ref> Similarly, the readily available ] was reacted with 3,3-dimethylallyl bromide and ] in THF solution, followed by reaction at with methyl iodide and ] in THF, yielding rosefuran.<ref>{{cite journal | author = Peter Weyerstahl | title = Structure-odor correlation. Part XXI. Olfactory properties and convenient synthesis of furans and thiophenes related to rosefuran and perillene and their isomers | journal = Liebigs Annalen | volume = 6 | pages = 1849–1853| year = 1995 |last2 = Schenk | first2 = Anja | last3 = Marschall | first3 = Helga | issue = 10 | doi=10.1002/jlac.1995199510259}}</ref> |
|
|
|
|
|
A patented process for the manufacture of rosefuran via condensation of 3-formylpropionic acid methyl ester with ] has been described. The intermediate ketoaldehyde is cyclized to a furan derivative which is converted to rosefuran in 33% overall yield via ] to give 2-methyl-4-(3-methyl-2-furanyl)-2-butanol followed by dehydration.<ref> Hidetaka Tsukasa, “Manufacture of rosefuran”, Jpn. Kokai Tokkyo Koho, 03151373 (1991)</ref> |
|
A patented process for the manufacture of rosefuran via condensation of 3-formylpropionic acid methyl ester with ] has been described. The intermediate ketoaldehyde is cyclized to a furan derivative which is converted to rosefuran in 33% overall yield via ] to give 2-methyl-4-(3-methyl-2-furanyl)-2-butanol followed by dehydration.<ref>Hidetaka Tsukasa, "Manufacture of rosefuran", Jpn. Kokai Tokkyo Koho, 03151373 (1991)</ref> |
|
|
|
|
|
== Applications == |
|
== Applications == |
|
Rosefuran is a desirable component of rose oil, a natural fragrance material.<ref>{{cite journal | author = Gunther Ohloff | title = Importance of minor components in flavors and fragrances | journal = Perfumer & Flavorist | volume = 3 | pages = 11-22 | year = 1978 | issue = 1}}</ref> Rosefuran is the major constituent (58% by weight) of the essential oil of ] ocimoides, a herbaceous, annual plant cultivated in ] and used as a component of a common spice.<ref>{{cite journal | author = L. N. Misra | title = The Essential Oil of Perilla ocimoides: A Rich Source of Rosefuran | journal = Planta medica | volume = 53 | pages = 379-380 | year = 1987 |last2 = Husain | first2 = A. | issue = 4}}</ref> Additionally, synthetic rosefuran is recommended (average recommended level in parentheses) for use as a flavor, fragrance chemical for a wide variety of applications including baked goods (5 ppm), breakfast cereal (2 ppm), cheese (3 ppm), condiments (2 ppm), frozen dairy (3 ppm), soups (2 ppm) and snack foods (5 ppm).<ref>rosefuran: http://www.thegoodscentscompany.com/data/rw1435551.html</ref> |
|
Rosefuran is a desirable component of rose oil, a natural fragrance material.<ref>{{cite journal | author = Gunther Ohloff | title = Importance of minor components in flavors and fragrances | journal = Perfumer & Flavorist | volume = 3 | pages = 11–22 | year = 1978 | issue = 1}}</ref> Rosefuran is the major constituent (58% by weight) of the essential oil of ''] ocimoides'', a herbaceous, annual plant cultivated in ] and used as a component of a common spice.<ref>{{cite journal | author = L. N. Misra | title = The Essential Oil of ''Perilla ocimoides'': A Rich Source of Rosefuran | journal = Planta Medica | volume = 53 | pages = 379–380 | year = 1987 |last2 = Husain | first2 = A. | issue = 4 | doi=10.1055/s-2006-962743 | pmid=17269047}}</ref> Additionally, synthetic rosefuran is recommended (average recommended level in parentheses) for use as a flavor, fragrance chemical for a wide variety of applications including baked goods (5 ppm), breakfast cereal (2 ppm), cheese (3 ppm), condiments (2 ppm), frozen dairy (3 ppm), soups (2 ppm) and snack foods (5 ppm).<ref>rosefuran: http://www.thegoodscentscompany.com/data/rw1435551.html</ref> |
|
|
|
|
|
== References == |
|
== References == |