Traumatic acid

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.

Traumatic acid^[1]

Names
Preferred 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 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL470062 N
ChemSpider	4446155 N
ECHA InfoCard	100.026.382
PubChem CID	5283028
UNII	L7ND24937H Y
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+ N Key: MAZWDMBCPDUFDJ-VQHVLOKHSA-N N
SMILES O=C(O)/C=C/CCCCCCCCC(O)=O
Properties
Chemical formula	C12H20O4
Molar mass	228.288 g·mol−1
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). N verify (what is YN ?) Infobox references

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

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)