CAS No. :	488-10-8
Formula :	C₁₁H₁₆O
M.W :	164.24
SMILES Code :	CC/C=C\CC1=C(C)CCC1=O
Synonyms :	cis-Jasmone; Jasmone; HSDB 8273
MDL No. :	MFCD00001402
InChI Key :	XMLSXPIVAXONDL-PLNGDYQASA-N
Pubchem ID :	1549018

Safety of cis-Jasmon

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of cis-Jasmon

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 488-10-8 ]

[ 488-10-8 ] Synthesis Path-Downstream 1~54

1
[ 488-10-8 ]
[ 10304-65-1 ]

References: [1]Helvetica Chimica Acta,1942,vol. 25,p. 1500,1512.

2
[ 488-10-8 ]
[ 136150-37-3 ]

References: [1]Chemische Berichte,1935,vol. 68,p. 642.

3
[ 488-10-8 ]
[ 119-26-6 ]
[ 5009-20-1 ]

References: [1]Helvetica Chimica Acta,1942,vol. 25,p. 1500,1512.

4
[ 67-56-1 ]
[ 488-10-8 ]
[ 64140-92-7 ]
3-Methyl-2-((E)-3-oxo-pent-1-enyl)-cyclopent-2-enone [ No CAS ]
2-(2-Hydroxy-3-oxo-pentyl)-3-methyl-cyclopent-2-enone [ No CAS ]
2-(1-Hydroxy-3-oxo-pentyl)-3-methyl-cyclopent-2-enone [ No CAS ]

References: [1]Bioscience, Biotechnology and Biochemistry,1993,vol. 57,p. 220 - 226.

5
[ 67-56-1 ]
[ 488-10-8 ]
(3aR,4S,5S,6aS)-4-Ethyl-5-methoxy-3a-methyl-hexahydro-pentalen-1-one [ No CAS ]
3-((1S,2R,3R)-2-Ethyl-3-methoxy-1-methyl-cyclopentyl)-propionic acid methyl ester [ No CAS ]
(1'R^*,2'R^*)-2-(2'-ethylcyclopropyl)-3-methyl-2-cyclopenten-1-one [ No CAS ]
(1'S^*,2'R^*)-2-(2'-ethylcyclopropyl)-3-methyl-2-cyclopenten-1-one [ No CAS ]

References: [1]Bioscience, Biotechnology and Biochemistry,1993,vol. 57,p. 220 - 226.

6
[ 81431-81-4 ]
[ 68776-91-0 ]
[ 488-10-8 ]

References: [1]Journal of Organic Chemistry,1987,vol. 52,p. 1440 - 1450.

7
[ 64-17-5 ]
[ 488-10-8 ]
[ 3726-51-0 ]
3-Methyl-2-((E)-2-oxo-pent-3-enyl)-cyclopent-2-enone [ No CAS ]
3-Methyl-2-((E)-3-oxo-pent-1-enyl)-cyclopent-2-enone [ No CAS ]
2-(1-Hydroxy-3-oxo-pentyl)-3-methyl-cyclopent-2-enone [ No CAS ]

References: [1]Bioscience, Biotechnology and Biochemistry,1993,vol. 57,p. 220 - 226.

8
[ 64-17-5 ]
[ 488-10-8 ]
(3aR,4S,5S,6aS)-5-Ethoxy-4-ethyl-3a-methyl-hexahydro-pentalen-1-one [ No CAS ]
3-((1S,2R,3R)-3-Ethoxy-2-ethyl-1-methyl-cyclopentyl)-propionic acid ethyl ester [ No CAS ]
(1'R^*,2'R^*)-2-(2'-ethylcyclopropyl)-3-methyl-2-cyclopenten-1-one [ No CAS ]
(1'S^*,2'R^*)-2-(2'-ethylcyclopropyl)-3-methyl-2-cyclopenten-1-one [ No CAS ]

References: [1]Bioscience, Biotechnology and Biochemistry,1993,vol. 57,p. 220 - 226.
[2]Bioscience, Biotechnology and Biochemistry,1993,vol. 57,p. 220 - 226.

9
[ 21676-03-9 ]
[ 69567-06-2 ]
[ 6407-36-9 ]
[ 488-10-8 ]

References: [1]Synthesis,1980,p. 413 - 416.

10
[ 41031-88-3 ]
[ 917-54-4 ]
[ 488-10-8 ]

References: [1]Synthetic Communications,1986,vol. 16,p. 871 - 876.

11
[ 7051-37-8 ]
[ 488-10-8 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1990,vol. 26,p. 1452 - 1455.
Zhurnal Organicheskoi Khimii,1990,vol. 26,p. 1678 - 1683.
[2]Journal of Organic Chemistry,1981,vol. 46,p. 4301 - 4304.
[3]Synthetic Communications,1986,vol. 16,p. 713 - 722.
[4]Chemical and pharmaceutical bulletin,1980,vol. 28,p. 349 - 351.
[5]Tetrahedron Letters,1996,vol. 37,p. 5735 - 5738.

12
[ 488-10-8 ]
[ 676-58-4 ]
[ 157562-89-5 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 6075 - 6078.

13
[ 488-10-8 ]
[ 1128-08-1 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 5594 - 5598.
[2]Tetrahedron,2005,vol. 61,p. 2217 - 2231.
[3]Chemistry - A European Journal,2007,vol. 13,p. 292 - 299.

14
[ 488-10-8 ]
[ 58282-77-2 ]
[ 64140-92-7 ]
[ 148694-03-5 ]
2-(1-Hydroxy-3-oxo-pentyl)-3-methyl-cyclopent-2-enone [ No CAS ]

References: [1]Bioscience, Biotechnology and Biochemistry,1993,vol. 57,p. 220 - 226.

15
[ 488-10-8 ]
[ 42050-67-9 ]

References: [1]Tetrahedron Letters,1991,vol. 32,p. 1741 - 1744.

16
[ 488-10-8 ]
[ 51906-25-3 ]
3-Methyl-2-((E)-3-oxo-pent-1-enyl)-cyclopent-2-enone [ No CAS ]
2-(2-Hydroxy-3-oxo-pentyl)-3-methyl-cyclopent-2-enone [ No CAS ]
2-(1-Hydroxy-3-oxo-pentyl)-3-methyl-cyclopent-2-enone [ No CAS ]

References: [1]Bioscience, Biotechnology and Biochemistry,1993,vol. 57,p. 220 - 226.

17
[ 488-10-8 ]
[ 3726-51-0 ]
3-Methyl-2-((E)-2-oxo-pent-3-enyl)-cyclopent-2-enone [ No CAS ]
3-Methyl-2-((E)-3-oxo-pent-1-enyl)-cyclopent-2-enone [ No CAS ]
2-(1-Hydroxy-3-oxo-pentyl)-3-methyl-cyclopent-2-enone [ No CAS ]

References: [1]Bioscience, Biotechnology and Biochemistry,1993,vol. 57,p. 220 - 226.

18
[ 488-10-8 ]
[ 165590-85-2 ]

References: [1]Tetrahedron Letters,1993,vol. 34,p. 257 - 260.
[2]Journal of Organic Chemistry,1994,vol. 59,p. 6378 - 6385.
[3]Chemistry Letters,1991,p. 1847 - 1848.

19
[ 488-10-8 ]
[ 23260-40-4 ]
[ 123-76-2 ]
[ 148694-04-6 ]
(1S,4S,6R)-6-Ethyl-1-(3-oxo-butyl)-5-oxa-bicyclo[2.1.1]hexan-2-one [ No CAS ]

References: [1]Bioscience, Biotechnology and Biochemistry,1993,vol. 57,p. 220 - 226.
[2]Bioscience, Biotechnology and Biochemistry,1993,vol. 57,p. 220 - 226.

20
[ 488-10-8 ]
2-((E)-3-Hydroxy-pent-1-enyl)-3-methyl-cyclopent-2-enone [ No CAS ]
2-((E)-2-Hydroxy-pent-3-enyl)-3-methyl-cyclopent-2-enone [ No CAS ]
2-((E)-3-Hydroperoxy-pent-1-enyl)-3-methyl-cyclopent-2-enone [ No CAS ]
2-((E)-2-Hydroperoxy-pent-3-enyl)-3-methyl-cyclopent-2-enone [ No CAS ]

References: [1]Bioscience, Biotechnology and Biochemistry,1993,vol. 57,p. 220 - 226.

21
[ 488-10-8 ]
(1'R^*,2'R^*)-2-(2'-ethylcyclopropyl)-3-methyl-2-cyclopenten-1-one [ No CAS ]
(1'S^*,2'R^*)-2-(2'-ethylcyclopropyl)-3-methyl-2-cyclopenten-1-one [ No CAS ]

References: [1]Bioscience, Biotechnology and Biochemistry,1993,vol. 57,p. 220 - 226.

22
[ 4868-21-7 ]
[ 488-10-8 ]

References: [1]Bulletin of the Chemical Society of Japan,1992,vol. 65,p. 1257 - 1261.
[2]Bioscience, Biotechnology and Biochemistry,1994,vol. 58,p. 1181 - 1182.
[3]Tetrahedron Letters,1987,vol. 28,p. 4411 - 4414.
[4]Tetrahedron Letters,1988,vol. 29,p. 3587 - 3590.
[5]Synthetic Communications,1984,vol. 14,p. 469 - 476.
[6]Polish Journal of Chemistry,1983,vol. 57,p. 1047 - 1050.
[7]Journal of Organic Chemistry,2018.
[8]Tetrahedron,1981,vol. 37,p. 307 - 310.
[9]Bulletin of the Chemical Society of Japan,1981,vol. 54,p. 505 - 508.
[10]Australian Journal of Chemistry,1982,vol. 35,p. 1739 - 1741.
[11]Tetrahedron,1983,vol. 39,p. 4127 - 4132.
[12]Synthetic Communications,1989,vol. 19,p. 575 - 584.
[13]Tetrahedron Letters,1990,vol. 31,p. 2783 - 2786.
[14]Bulletin of the Chemical Society of Japan,1984,vol. 57,p. 1691 - 1692.
[15]Chemistry Letters,1984,p. 1795 - 1798.

23
[ 4868-21-7 ]
[ 488-10-8 ]
[ 6261-18-3 ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 4002 - 4005.

24
[ 58282-77-2 ]
[ 6228-47-3 ]
[ 488-10-8 ]

References: [1]Synthetic Communications,1985,vol. 15,p. 1147 - 1152.

25
[ 53376-48-0 ]
[ 488-10-8 ]

References: [1]Gazzetta Chimica Italiana,1984,vol. 114,p. 327 - 330.

26
[ 128192-01-8 ]
[ 488-10-8 ]

References: [1]Journal of the Chemical Society. Chemical communications,1990,p. 684 - 686.
[2]Journal of Organic Chemistry,1990,vol. 55,p. 5294 - 5297.

27
[ 488-10-8 ]
[ 108-24-7 ]
[ 123-76-2 ]
[ 148694-04-6 ]
Acetic acid 2-acetoxy-1-(5-methyl-2-oxo-6-oxa-bicyclo[3.1.0]hex-1-ylmethyl)-butyl ester [ No CAS ]

References: [1]Bioscience, Biotechnology and Biochemistry,1993,vol. 57,p. 220 - 226.

28
[ 488-10-8 ]
[ 108-24-7 ]
[ 123-76-2 ]
[ 148694-04-6 ]
Acetic acid 2-acetoxy-1-(5-methyl-2-oxo-6-oxa-bicyclo[3.1.0]hex-1-ylmethyl)-butyl ester [ No CAS ]
Acetic acid (2R,3aR,6aR)-2-(1-acetoxy-propyl)-6a-methyl-4-oxo-hexahydro-cyclopenta[b]furan-3a-yl ester [ No CAS ]

References: [1]Bioscience, Biotechnology and Biochemistry,1993,vol. 57,p. 220 - 226.

29
[ 132604-79-6 ]
[ 488-10-8 ]

References: [1]Journal of Organic Chemistry,1992,vol. 57,p. 1170 - 1178.
[2]Tetrahedron Letters,1990,vol. 31,p. 6145 - 6148.

30
[ 32556-66-4 ]
[ 488-10-8 ]
[ 6261-18-3 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1990,vol. 26,p. 1452 - 1455.
Zhurnal Organicheskoi Khimii,1990,vol. 26,p. 1678 - 1683.

31
[ 79155-17-2 ]
[ 488-10-8 ]

References: [1]Tetrahedron Letters,1981,vol. 22,p. 2447 - 2450.

32
[ 32556-66-4 ]
[ 488-10-8 ]

References: [1]Tetrahedron,1983,vol. 39,p. 2421 - 2428.

33
[ 106763-43-3 ]
[ 488-10-8 ]

References: [1]Journal of Organic Chemistry,1987,vol. 52,p. 1440 - 1450.

34
2-((4R,5S)-5-Ethyl-2-methoxy-[1,3]dioxolan-4-ylmethyl)-3-methyl-cyclopent-2-enone [ No CAS ]
[ 488-10-8 ]

References: [1]Chemistry Letters,1986,p. 879 - 882.

35
[ 73959-78-1 ]
[ 488-10-8 ]

References: [1]Bulletin of the Chemical Society of Japan,1980,vol. 53,p. 169 - 173.

36
[ 925-90-6 ]
[ 79858-12-1 ]
[ 74-86-2 ]
[ 488-10-8 ]

References: [1]Chemistry Letters,1981,p. 1189 - 1192.

37
[ 488-10-8 ]
[ 75-24-1 ]
[ 157562-89-5 ]

References: [1]Synthesis,1995,p. 317 - 320.

38
[ 488-10-8 ]
[ 74-88-4 ]
[ 58256-67-0 ]

References: [1]Synthetic Communications,1975,vol. 5,p. 435 - 439.

39
[ 488-10-8 ]
(2S,3S)-3-Methyl-2-((Z)-pent-2-enyl)-cyclopentanone [ No CAS ]
(2S,3R)-3-Methyl-2-((Z)-pent-2-enyl)-cyclopentanone [ No CAS ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 2928 - 2929.

40
[ 488-10-8 ]
[ 1774-47-6 ]
5-methyl-1-(pent-2'-enyl)bicyclo<3.1.0>hexan-2-one [ No CAS ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 8885 - 8896.

41
[ 488-10-8 ]
1-(pent-2'-enyl)-5-methyl-6-oxabicyclo[3.1.0]hexan-2-one [ No CAS ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 8885 - 8896.

42
1-(pent-2'-enyl)-5-methyl-6-oxabicyclo[3.1.0]hexan-2-one [ No CAS ]
[ 488-10-8 ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 8885 - 8896.

43
[ 165590-85-2 ]
[ 488-10-8 ]

References: [1]Journal of the Chinese Chemical Society,1998,vol. 45,p. 319 - 321.

Yield	Reaction Conditions	Operation in experiment
73%		EXAMPLE 5 Invention 0.4 g (2.5 millimole) of the final product of Example 4 was dissolved in 1 ml of tetrahydrofuran. 20 ml of NH4 OH was added and the mixture was stirred for 12 hours. Dilution with water and extraction with ether produced a crude product which was purified by flash column chromatography to yield 0.3 g (73% yield) of 2-(cis-2-pentenyl)-3-methyl-2-cyclopenteneone (commonly known as cis-jasmone): STR10

46
(+-)-2.5-dioxo-undecene-(8c)-carboxylic acid-⁽⁴⁾-methyl ester [ No CAS ]
[ 488-10-8 ]

References: [1]Chemische Berichte,1942,vol. 75,p. 467.
Chemische Berichte,1947,vol. 80,p. 142.

47
1-methyl-2-<pentadien-(2c.4)-yl>-cyclopenten-(1)-one-(3) [ No CAS ]
[ 488-10-8 ]

References: [1]Journal of the Chemical Society,1945,p. 412.

48
4-hydroxy-4-methyl-5-ethoxycarbonyl-decen-(7c)-oic acid ⁽¹⁾-lactone [ No CAS ]
[ 488-10-8 ]

References: [1]Chemische Berichte,1935,vol. 68,p. 642.

49
5-hydroxy-1-methyl-2-<pentadien-(2.4)-yl>-cyclopenten-(1)-one-(3) [ No CAS ]
[ 488-10-8 ]

References: [1]Journal of the Chemical Society,1945,p. 412.

50
[ 74-85-1 ]
hexacarbonyl(oct-4(Z)-en-1-yne)dicobalt [ No CAS ]
[ 488-10-8 ]

References: [1]Journal of Chemical Research, Miniprint,1988,p. 2601 - 2623.

51
[ 82909-46-4 ]
lithium dimethylcuprate [ No CAS ]
[ 488-10-8 ]

References: [1]Canadian Journal of Chemistry,1982,vol. 60,p. 1256 - 1263.

52
[ 207798-52-5 ]
[ 488-10-8 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 7714 - 7722.

53
[ 488-10-8 ]
[ 917-54-4 ]
[ 157562-89-5 ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 141 - 143.

54
[ 488-10-8 ]
[ 7051-39-0 ]

References: [1]Organic Letters,2003,vol. 5,p. 2417 - 2420.

Historical Records

Technical Information

• Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • Grignard Reaction • Halogenation • Heat of Combustion • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 488-10-8

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CAS No.: 488-10-8

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[ 488-10-8 ] Synthesis Path-Downstream 1~54

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