L-hydroxyproline, also known as Trans-4-hydroxy-L-proline or Trans-Hyp, is extensively utilized in the food, cosmetic, biochemistry, medical, and other industries. Furthermore, it has been discovered that several secondary metabolites, like actinomycins and echinocandins, include L-hydroxyproline. Because it is abundant in collagen, L-hydroxyproline is mostly produced industrially by acid hydrolyzing mammalian collagen[1].

[1]. Biosynthesis of trans-4-hydroxyproline by recombinant strains of Corynebacterium glutamicum and Escherichia coli. BMC Biotechnol. 2014 May 19;14:44.

Trans-4-hydroxy-L-proline is an optically active form of 4-hydroxyproline, exhibiting the L-trans configuration. It is found in humans, plants, and mice, and is a zwitterion tautomer of trans-4-hydroxy-L-proline. Hydroxyproline is a neutral heterocyclic protein amino acid found in collagen and is therefore commonly found in many gelatin products. Hydroxyproline is primarily used as a diagnostic marker for bone turnover and liver fibrosis. In terms of treatment, hydroxyproline is being investigated as an experimental drug, but it has been approved in France for the treatment of small, superficial wounds, in a compound topical gel product called Cicactive. Hydroxyproline is a metabolite found in or produced by Escherichia coli (K12 strain, MG1655 strain). 4-Hydroxy-L-proline is a metabolite found in or produced by Escherichia coli (K12 strain, MG1655 strain). Hydroxyproline has been reported in Daphnia pulex, Glycine max, and other organisms with relevant data. Hydroxyproline is a non-essential amino acid derivative formed during post-translational modification of proteins by the hydroxylation of the amino acid proline by prolyl hydroxylase, an enzyme that requires vitamin C as a cofactor. Hydroxyproline is a major component of collagen and plays a crucial role in maintaining the stability of the collagen triple helix structure. Hydroxyproline can be used as an indicator of collagen content. Elevated levels of hydroxyproline in urine and/or serum are often associated with connective tissue degradation. Vitamin C deficiency reduces the conversion of proline to hydroxyproline, leading to decreased collagen stability. 4-Hydroxyproline (or hydroxyproline or Hyp) is a major component of collagen. Hydroxyproline is generated by the hydroxylation of the amino acid proline, and is therefore a post-translational modified amino acid. Hydroxyproline and proline play crucial roles in maintaining collagen stability. In particular, they can cause significant distortion of the collagen helix. Hydroxyproline is rarely found in other proteins besides collagen. The only protein in mammals containing hydroxyproline is elastin. Therefore, hydroxyproline content has been used as an indicator of collagen and/or gelatin content in tissue or biological samples. Serum and urine hydroxyproline levels are elevated in patients with Paget's disease. Hydroxyproline (Hyp) content in bodily fluids has been used as an indicator of collagen catabolism, particularly related to bone resorption or tissue degradation. Serum hydroxyproline levels are significantly higher in bedridden and elderly individuals than in normally active individuals. Elevated urinary hydroxyproline levels also suggest muscle damage. Increased reactive oxygen species (ROS) are known to accelerate collagen degradation. Hydroxyproline levels are also elevated under conditions of depression and stress (A3486, A3487, A3488, A3489). See also: Hydroxyproline; Octyl methoxycinnamate (ingredient); Hydroxyproline; Nicotinamide (ingredient)... See more...

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Drug Indications
In France, this product is used as a compound preparation for the treatment of small, superficial wounds.

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Pharmacodynamics
Hydroxyproline, along with proline and glycine, are major components of collagen. Collagen is one of the main components of connective tissues such as skin, bones, and cartilage. Therefore, when these tissues are damaged, hydroxyproline is essential for repairing damaged areas.

C5H9NO3

131.13

131.058

51-35-4

25249-07-4

5810

White to off-white solid powder

1.4±0.1 g/cm3

355.2±42.0 °C at 760 mmHg

273 °C (dec.)(lit.)

168.6±27.9 °C

0.0±1.8 mmHg at 25°C

1.540

-1.84

3

4

1

9

125

2

O([H])C1([H])C([H])([H])N([H])[C@]([H])(C(=O)O[H])C1([H])[H]

PMMYEEVYMWASQN-DMTCNVIQSA-N

InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1

(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid

NSC 46704; Oxaceprol; Hydroxyproline

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

H2O : ~50 mg/mL (~381.30 mM)

Solubility in Formulation 1: 100 mg/mL (762.60 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

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 (Please use freshly prepared in vivo formulations for optimal results.)