LBF18305SC01

Upper classes: LB LBF

(9Z,11E,13Z) -Octadecatrienoic acid

Structural Information
	(cis-9,trans-11,cis-13) -Octadecatrienoic acid
	(9Z,11E,13Z) -Octadecatrienoic acid Punicic acid Trichosanic acid

Formula	C18H30O2
Exact Mass	278.224580204
Average Mass	278.4296
SMILES	`CCCCC=CC=CC=CCCCCCCCC(O)=O`
Physicochemical Information
	43.5-44°C

	d50 4 0.9025

	1.5113 at 50°C
	soluble in ethanol, pentane and petroleum ether. Chisholm_MJ et al.
	Seed oils of Punica granatum (pomegranate) and Catalpa speciosa; Chilopsis sp.; C. linearis.





Spectral Information
Mass Spectra
UV Spectra
IR Spectra
NMR Spectra
Other Spectra
Chromatograms

Reported Metabolites, References

Biospecies	ID	Compound Name	Reference	Comment
n.a.	LBF18305SC01	See above.	Chisholm_MJ et al. 1962

There are 8 possible isomers, and 4 are naturally identified.

３つある二重結合の構造異性体は８種類考えられるが、４種が天然に見つかっている。

α-eleostearic acid (cis, trans, trans) LBF18305SC02 m.p. 48 °C

The most common acid of this group. Principal acid of tung oil or China Wood oil, and the seed oil of Momordica charantia and Centranthus macrosiphon. It is easily converted to β-eleostearic acid by light, heat, sulfur, acid, or iodine.

もっとも一般的で、ツング（中国では四川省に生える油桐）油、 Momordica charantia や Centranthus macrosiphon の種から取れる油の主成分。光や熱、硫黄、酸、ヨウ素などによって容易に β-eleostearic acid に変化する。

Punicic acid (cis, trans, cis) LBF18305SC01 m.p. 41 °C

Principal acid of pomegranate seed oil. Yellow. It is easily coverted to β-eleostearic acid by the same catalysts. Its alternative name is Trichosanic acid, a major component of Trichosanthes kirilowii japonica seed oil. It shows platelet aggregation ^[1]

In a recent article^[2], (trans, cis, trans)-form was isolated from pomegranate (Punica granatum seed and it constituted about 88% of the seed oil.

The result contradicts other results (Punicic acid is major, e.g. ^[3]), and is considered an error. (By:Masanori Arita)

ザクロの種から取れる黄色い油の主成分。ザクロの属名 Punica より名がついている。 α-eleostearic acidと同様に、同じ触媒によって簡単に β-eleostearic acid に変化する。別名は Trichosanic acid で、日本のでヘビウリと呼ばれる Trichosanthes kirilowii japonica 種子の主成分。血小板の凝固作用がある。

最近の文献では (trans, cis, trans)-型がザクロPunica granatum)種子油の主成分で88%を占めると報告されている。この結果はこれまでの研究(Punicic acid が主成分と異なるため、間違いではないかと思われる。 (By:有田正規)

β-eleostearic acid (trans, trans, trans) LBF18305SC03 m.p. 72 °C

Transformed form of α-eleostearic acid or punicic acid.

α-eleostearic acid や punicic acid が変化したもの。

Catalpic acid (trans, trans, cis) m.p. 32 °C

Principal acid of Catalpa ovata, Catalpa speciosa and Catalpa bignonioides seed oil.

Catalpa ovata, Catalpa speciosa や Catalpa bignonioides 種子油の主成分。

References

↑ Takenaga M, Hirai A, Terano T, Tamura Y, Kitagawa H, Yoshida S (1988) "In vitro effect of trichosanic acid, a major component of Trichosanthes japonica on platelet aggregation and arachidonic acid metabolism in human platelets" Prostaglandins Leukot Essent Fatty Acids 31(2):65-72
↑ Fatope MO, Al Burtomani SK, Takeda Y (2002) "Monoacylglycerol from Punica granatum Seed Oil" J Agric Food Chem 50:357-360
↑ Kyralan M, Golukcu M, Tokgoz H (2009) "Oil and Conjugated Linolenic Acid Contents of Seeds from Important Pomegranate Cultivars (Punica granatum L.) Grown in Turkey" J Am Oil Chem Soc 86:985–990

[1] Takenaga M, Hirai A, Terano T, Tamura Y, Kitagawa H, Yoshida S (1988) "In vitro effect of trichosanic acid, a major component of Trichosanthes japonica on platelet aggregation and arachidonic acid metabolism in human platelets" Prostaglandins Leukot Essent Fatty Acids 31(2):65-72

[2] Fatope MO, Al Burtomani SK, Takeda Y (2002) "Monoacylglycerol from Punica granatum Seed Oil" J Agric Food Chem 50:357-360

[3] Kyralan M, Golukcu M, Tokgoz H (2009) "Oil and Conjugated Linolenic Acid Contents of Seeds from Important Pomegranate Cultivars (Punica granatum L.) Grown in Turkey" J Am Oil Chem Soc 86:985–990

[1]

[2]

[3]

IDs and Links
LipidBank	DFA0185
LipidMaps	LMFA01030146
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}

mol	LBF18305SC01

LBF18305SC01

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