cis-4-Hydroxy-L-proline, a proline analogue, is an inhibitor (blocker/antagonist) of collagen production. cis-4-Hydroxy-L-proline inhibits fibroblast growth by preventing the deposition of triple-helical collagen on the cell layer. cis-4-Hydroxy-L-proline also suppresses the growth of primary N-nitrosomethylurea-induced rat mammary tumors.

Physicochemical Properties

Molecular Formula	C5H9NO3
Molecular Weight	131.13
Exact Mass	131.058
CAS #	618-27-9
Related CAS #	cis-4-Hydroxy-L-proline-d3
PubChem CID	440015
Appearance	White to off-white solid powder
Density	1.4±0.1 g/cm3
Boiling Point	355.2±42.0 °C at 760 mmHg
Melting Point	257ºC
Flash Point	168.6±27.9 °C
Vapour Pressure	0.0±1.8 mmHg at 25°C
Index of Refraction	1.540
LogP	-1.84
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	1
Heavy Atom Count	9
Complexity	125
Defined Atom Stereocenter Count	2
SMILES	C1[C@@H](CN[C@@H]1C(=O)O)O
InChi Key	PMMYEEVYMWASQN-IMJSIDKUSA-N
InChi Code	InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m0/s1
Chemical Name	(2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

References

[1]. Sensitivity of N-nitrosomethylurea-induced rat mammary tumors to cis-hydroxyproline, an inhibitor of collagen production. Cancer Res. 1981 Jul;41(7):2855-62. [2]. Proline analogue removes fibroblasts from cultured mixed cell populations. Nature. 1977 Mar 3;266(5597):63-4. [3]. Proline analogues inhibit human skin fibroblast growth and collagen production in culture. J Invest Dermatol. 1983 Apr;80(4):261-7. [4]. Prevention of bleomycin-induced pulmonary fibrosis in the hamster by cis-4-hydroxy-l-proline. Am Rev Respir Dis. 1981 Apr;123(4 Pt 1):388-93.

Additional Infomation

Cis-4-hydroxy-L-proline is l-Proline in which a hydrogen at the 4-position of the pyrrolidine ring is substituted by a hydroxy group (S-configuration). It has a role as a metabolite. It is a non-proteinogenic L-alpha-amino acid and a 4-hydroxyproline. It is a tautomer of a cis-4-hydroxy-L-proline zwitterion. cis-4-Hydroxyproline has been reported in Festuca ovina, Festuca pratensis, and other organisms with data available. A hydroxylated form of the imino acid proline. A deficiency in ASCORBIC ACID can result in impaired hydroxyproline formation.

Solubility Data

Solubility (In Vitro)	H2O :~100 mg/mL (~762.60 mM) DMSO :< 1 mg/mL
Solubility (In Vivo)	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.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	7.6260 mL	38.1301 mL	76.2602 mL
	5 mM	1.5252 mL	7.6260 mL	15.2520 mL
	10 mM	0.7626 mL	3.8130 mL	7.6260 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.