Traumatic acid

Traumatic acid[1]
Names
	IUPAC name (2E)-Dodec-2-enedioic acid
	Other names (E)-Dodec-2-enedioic acid; Dodec-2-enedioic acid; trans-Traumatic acid
Identifiers
CAS Number	6402-36-4 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL470062 ;
ChemSpider	4446155 ;
ECHA InfoCard	100.026.382
PubChem CID	5283028;
UNII	L7ND24937H ;
CompTox Dashboard (EPA)	DTXSID00863778 ;
	InChI InChI=1S/C12H20O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h7,9H,1-6,8,10H2,(H,13,14)(H,15,16)/b9-7+ Key: MAZWDMBCPDUFDJ-VQHVLOKHSA-N ;
	SMILES O=C(O)/C=C/CCCCCCCCC(O)=O;
Properties
Chemical formula	C12H20O4
Molar mass	228.28
Melting point	166 to 167 °C (331 to 333 °F; 439 to 440 K)
Boiling point	150 to 160 °C (302 to 320 °F; 423 to 433 K) at 0.001 mmHg
Solubility in water	Sparingly soluble
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Traumatic acid is a monounsaturated dicarboxylic acid that occurs naturally in plants. The compound was first isolated from wounded bean plants by American chemists James English Jr. and James Frederick Bonner and Dutch scientist Arie Jan Haagen-Smit in 1939.[2] Traumatic acid is a potent wound healing agent in plants ("wound hormone") that stimulates cell division near a trauma site to form a protective callus and to heal the damaged tissue. It may also act as a growth hormone, especially in inferior plants (e.g. algae). Traumatic acid is biosynthesized in plants by non-enzymatic oxidation of traumatin (12-oxo-trans-10-dodecenoic acid), another wound hormone.

At normal conditions, traumatic acid is a solid, crystalline, water-insoluble substance. The salts and esters of traumatic acid are called traumatates.

Traumatic acid is used as an intermediate in prostaglandin synthesis. It is also a constituent of some pharmaceutical products, such as the odontostomatologic gel Restomyl, due to its mucosal re-epithelialization activity.

References

Merck Index, 11th Edition, 9493
English J Jr., Bonner J, Haagen-Smit AJ: Structure and synthesis of a plant wound hormone. Science 90:329. (1939)

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[1] Merck Index, 11th Edition, 9493

[2] English J Jr., Bonner J, Haagen-Smit AJ: Structure and synthesis of a plant wound hormone. Science 90:329. (1939)