Traumatic acid

Traumatic acid

Chembox new
Reference = ["Merck Index", 11th Edition, 9493]
ImageFile = Traumatic acid structure.png ImageSize = 250px
IUPACName = Dodec-2-enedioic acid
OtherNames = "trans"-Traumatic acid
Section1 = Chembox Identifiers
CASNo = 6402-36-4
PubChem = 5283028
SMILES = O=C(O)/C=C/CCCCCCCCC(O)=O
Section2 = Chembox Properties
Formula = C12H20O4
MolarMass = 228.28
Appearance =
Density =
MeltingPt = 166-167 °C
BoilingPt = 150-160 °C at 0.001 mmHg
Solubility = Sparingly soluble
Section3 = Chembox Hazards
MainHazards =
FlashPt =
Autoignition =

Traumatic acid is a monounsaturated dicarboxylic acid naturally occurring 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. [English J Jr., Bonner J, Haagen-Smit AJ: Structure and synthesis of a plant wound hormone. "Science" 90:329. (1939)] 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-dodecanoic acid), another wound hormone.

At normal conditions, traumatic acid is a solid, crystalline, water insoluble substance.

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


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