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Long chain aldehyde


DATA No : DLD0006 INFORMANT : Toshihide Suzuki

NAME : 2,4-hexadienal

COMMON NAME: sorbic aldehyde/sorbaldehyde
SYMBOL:
FORMULA: C6H8O MOL.WT (average) : 96.127


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BIOLOGICAL ACTIVITY
E,E-form: Severe eye and skin irritant.
LD50(rat, orl) 730mg/kg(Ref. 0008) LD50(rat, orl) 300mg/kg(Ref. 0008)(Ref. 0109) LD50(rbt, skn) 270mg/kg(Ref. 0008)(Ref. 0109)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:E,E-form Mp -18deg(Ref. 0010)

BOILING POINT:2Z,4E-form Bp760 180deg(Ref. 0009) Bp20 68-68.5deg(Ref. 0011) E,E-form Bp173-174deg/ Bp11 64-66deg(Ref. 0109)

REFRACTIVE INDEX:n 1.535(Ref. 0008) nd-27 1.5367(Ref. 0011)

OPTICAL ROTATION:

DENSITY:d 0.89(Ref. 0008)(Ref. 0011)

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:E,E,-form lmax(in ethanol) 271nm(Ref. 0010) lmax(in 95% ethanol) 271.5nm(Ref. 0011)

IR SPECTRA:2Z,4E-form u 3040, 2960, 1670, 1640, 1580 cm-1(Ref. 0009) E,E-form u 3035, 3026, 3010, 3004, 2982, 2968, 2938, 2914, 2882, 2850, 2820, 2808, 2734, 1680, 1639, 1603, 1590, 1448, 1435, 1394, 1378, 1303, 1292, 1230, 1214, 1166, 1120, 1085, 1035, 1014, 988, 926, 863, 777, 612, 504, 480, 375, 298, 285, 242, 200, 145, 126 cm-1(Ref. 0010)

NMR SPECTRA:2Z,4E-form 1H NMR: d 1.92(d, 3H), 5.60-7.30(m, 4H), 10.17(d, 1H)(Ref. 0009) E,E-form 1H NMR (CDCl3, 200MHz): d 1.88(d, 3H), 6.04(dd, 1H), 6.42(m, 2H), 7.22(m, 1H), 9.54(d, 1H)(Ref. 0048)

MASS SPECTRA:2Z,4E-form m/z 96(M+), 81, 67, 53(Ref. 0009)

OTHER SPECTRA:
Raman spectrum E,E-form 3035, 3026, 3004, 2982, 2968, 2938, 2914, 2882, 2850, 2820, 2807, 2734, 1680, 1639, 1603, 1590, 1448, 1435, 1394, 1378, 1303, 1292, 1230, 1214, 1166, 1120, 1085, 1035, 1014, 988, 926, 863, 777, 612, 375, 298, 242, 200, 126(Ref. 0010)
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE
Polymerizes explosively on heating.(Ref. 0109)
REFERENCES
[0008]
AUTHOR:Ford,R.A.
TITLE:trans, trans-2,4-Hexadienal. PubMed ID:3391463
JOURNAL:Food Chem. Toxicol.
VOL:26 PAGE : 337 -337 (1988)
[TOP]

[0009]
AUTHOR:Furber,M., Herbert,J.M., and Taylor,R.J.K.
TITLE:Stereoselective Synthesis of 2Z, 4E-Dienals by Addition of Organometallic Reagents to Pyrylium Perchlorate
JOURNAL:J. Chem. Soc. Perkin I
VOL: PAGE : 683 -690 (1989)
[TOP]

[0010]
AUTHOR:Abo Aly,M.M., Baron,M.H., Favrot,J., Belloc,J., and Revault,M.
TITLE:Vibrational Analysis of (E,E)-2,4-Hexadienal, (E,E,E)-2,4,6-Octatrienal, and (E,E,E)-3-Methyl-2,4,6-Octatrienal
JOURNAL:Can. J. Chem.
VOL:63 PAGE : 1587 -1593 (1985)
[TOP]

[0011]
AUTHOR:Pippen,E.L., and Nonaka,M.
TITLE:A Convenient Method for Synthesizing Normal Aliphatic 2,4-Dienals
JOURNAL:J. Org. Chem.
VOL:23 PAGE : 1580 -1582 (1958)
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[0048]
AUTHOR:Bellassoued,M., nad Majidi,A.
TITLE:A Simple and Highly Stereoselective Route to E-a,b-Unsaturated Aldehydes
JOURNAL:J. Org. Chem.
VOL:58 PAGE : 2517 -2522 (1993)
[TOP]

[0109]
AUTHOR:Dictionary of Organic Compounds Sixth Edition, pp3452 (1996), Champan and Hall, London
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.