L-Hydroxyproline CAS 51-35-4

Molecular Formula: C5H9NO3

Formula Weight: 131.13

ZSpharmac: L-Hydroxyproline Supplement

Product Name: L-Hydroxyproline

CAS No: 51-35-4

Purity: 99%

Basic Info

Product Name:	L-Hydroxyproline
Other Names:	Trans-4-Hydroxy-L-Proline, 99+%
CAS:	51-35-4
Place of Origin:	Shandong, China
Brand Name:	ZSpharmac
Type:	Active Pharmaceutical Ingredients
Appearance:	White Crystals or Crystalline Powder
EINECS No.:	262-390-0
Storage:	Store Below +30°C.
Provide:	L-Hydroxyproline MSDS； L-Hydroxyproline COA

What is L-Hydroxyproline?

L-Hydroxyproline is a common non-standard protein amino acid. It is produced by the interaction of proline with ascorbic acid vitamin C. This process produces a hydroxyl group bound to a hydrogen-oxygen molecule, which is attached to a carbon molecule of proline and converted to hydroxyproline.
This amino acid was first isolated from a gel in 1902. It is one of the 22 amino acids required to make up human protein and is part of the standard human genetic code. Hydroxyproline is produced in the gastrointestinal tract.
Hydroxyproline cannot be produced without vitamin C. Without it, it can also cause serious problems because the body also cannot produce collagen, the most important protein structure. Both proline and hydroxyproline are important for the formation of this key substance, and a lack of either can lead to severe instability of collagen in the body. A lack of this amino acid is often the earliest visible symptom of scurvy. The most fundamental cause of scurvy is a lack of vitamin C, but it is manifested through a lack of collagen, which is directly related to insufficient hydroxyproline secretion. Without it, human collagen becomes unstable and excreted in urine. A lack of collagen can lead to easy bruising of the skin, damage to connective tissue, and the potential for internal bleeding. Additionally, a lack of this amino acid can cause hair loss and gum recession.
Besides collagen, the only mammalian protein produced using hydroxyproline is elastin. As the name suggests, this is a protein responsible for providing skin elasticity. This mechanism ensures that the body does not cause deformities during stress and movement. But a lack of hydroxyproline can also cause this protein deficiency, but not as quickly or dramatically as collagen.
It is not necessary to obtain this amino acid from the diet. Its precursor form, proline, is also a non-essential amino acid that can be produced by the body itself. However, vitamin C is an important nutrient for the human body, and most of it must be consumed through fruits and vegetables for proper function of the human body.
As the main raw material of antiviral drug atazanavir, it has high application value. L-Hydroxyproline is generally used as a food additive (used as a sweetener with a relatively small amount), and a relatively large amount of intermediates used as penem side chains in medicine.

L-Hydroxyproline Properties:

Melting point	273 °C (dec.)(lit.)
alpha	-75.5 º (c=5, H2O)
Boiling point	242.42°C (rough estimate)
density	1.3121 (rough estimate)
vapor density	4.5 (vs air)
refractive index	-75.5 ° (C=4, H2O)
storage temp.	Store below +30°C.
solubility	H₂O: 50 mg/mL
form	Crystals or Crystalline Powder
pka	1.82, 9.66(at 25℃)
color	White
PH	5.5-6.5 (50g/l, H2O, 20℃)
Odor	Odorless
optical activity	[α]25/D 75.6°, c = 1 in H2O
Water Solubility	357.8 g/L (20 º C)

L-Hydroxyproline Uses

L-Hydroxyproline Flavour Enhancer; Nutritional Enhancer. fragrance. Primarily used for fruit juices, refreshing beverages, nutritional beverages, and so on; utilized as a biochemical reagent.
L-Hydroxyproline is a versatile reagent for the synthesis of neural excitatory kainoid antifungal echinocandins and also for the synthesis of chiral ligands that can be used for asymmetric ethylation of aldehydes.

The Preparation Method of L-Hydroxyproline

A preparation method of L-hydroxyproline, specifically comprising the steps:
step one,
100 g of pyroglutamic acid alcohol, 16.5 g of p-toluenesulfonic acid monohydrate, 130 g of benzaldehyde, and 350 g of toluene were added to a 2L reaction flask in turn, heated to 70-120 °C for 4-6 hours, and then concentrated under reduced pressure to evaporate the solvent toluene. The obtained oil was purified by column chromatography to obtain 40.5g of TSSA0200-A, HPLC: 95%, yield 23%;
Step two,
Take 30g of TSSA0200-A, add 900ml of tetrahydrofuran, add 90g of MoOPH to a 2L reaction flask, under nitrogen protection, warm to -40～-50℃, add 240g of LiHMDS dropwise, react for 6～10h, quench the reaction, and obtain 9.7 by column chromatography g TSSA0200-B, HPLC: 94.2%, yield: 30%;
Step three,
Add 5g of TSSA0200-B into a 100ml three-necked flask, add 50ml of tetrahydrofuran under nitrogen protection, cool down to -15～-20°C, add 0.8g of tetrahydroaluminum lithium, warm up to room temperature and react for 6～8h, quench the reaction, and perform column chromatography 1.5g of TSSA0200-C was obtained, HPLC: 97%, yield: 31.7%;
Step 4.
Dissolve 1.5 g of TSSA0200-C with 30 ml of ethanol, add it to an autoclave, add 0.015 g of palladium carbon, pass hydrogen to 1 MPa, react for 3 h, and remove the palladium carbon by filtration to obtain 0.82 g of TSSA0200-D, yield: 96.5%;
Step 5.
0.082g of TEMPO was prepared into a 20wt% solution, 0.82g of TSSA0200-D was prepared into a 10wt% solution, pumped into a silica gel column to react for 5-10min to obtain a solution of TSSA0200-D, and 0.6g L- Hydroxyproline, yield 65.4%.

Method for Preparing L-Hydroxyproline by Enzymatic Hydrolysis

The method for preparing L-hydroxyproline by enzymatic hydrolysis comprises the following steps:
S1, the culture tank is first sterilized, then the liquid culture medium is put into the culture tank, and then inoculated;
S2. Insert the L-proline producing strain into the culture tank, the inoculation temperature is 30°C, pH 7.0, insert the needle of the inoculation bottle into the inoculation port, and after the inoculation is completed, place the cotton ball soaked in 75% ethanol on the On the inoculation port, pull out the inoculation needle and start the culture;
S3. Cultivation: the cultivation temperature is 30°C, the stirring speed is 200rpm, and the cultivation time is 8 hours. When the dissolved oxygen in the fermentation process rises to 10%, the glucose is started to flow, and the dissolved oxygen in the fermentation process is controlled at 10%, and the final glucose content is less than 10g. /L, strains are cultivated in liquid medium to obtain mature seeds;
S4. The mature seeds are transferred into the fermentation medium of the fermenter to ferment and metabolize to produce L-hydroxyproline. At the end of the fermentation, the production concentration of hydroxyproline is 30g/L, and the sugar concentration is less than or equal to 2.0%;
S5. Microfilter the L-hydroxyproline fermentation broth to obtain microfiltration liquid and microfiltration retentate, adjust the pH value of the microfiltration liquid to 6, then adsorb with a strongly acidic cation exchange resin, and then use a weakly basic anion The ion exchange liquid is obtained by the adsorption of the exchange resin, and the volume ratio of the strongly acidic cation exchange resin to the weakly basic anion exchange resin is 3:4;
S6. After decolorizing the microfiltrate with activated carbon at a temperature of 30°C, concentrate at 50°C until the volume is 1/8 to 1/6 of the volume before concentration, and centrifuge at a temperature of 20°C to obtain the finished product of L-hydroxyproline, and the excess mother liquor Carry out several times of strong acid cation exchange resin adsorption, and then use weak base anion exchange resin to adsorb to obtain ion exchange liquid, and repeat the operation to obtain the finished product of L-hydroxyproline.
In step S4, the fermentation medium is put into the fermenter, heated to 100°C with steam at a pressure of 0.1 MPa, maintained for 10 minutes, cooled to 35°C, adjusted to pH 6.5, and ready for inoculation.
The L-proline producing strain is Corynebacterium glutamicum.
Strong acid cation exchange resin is a cation exchange resin with sulfonic acid group on styrene-divinylbenzene copolymer. The weakly basic anion exchange resin is a polyacrylic anion exchange resin.

Detection of L-Hydroxyproline by Raman Spectroscopy

CN201810038019.3 provides a method that can improve the detection accuracy of L-hydroxyproline Raman spectrum, can reduce the interference of other substances on the Raman spectrum of L-hydroxyproline, and ensure the accuracy of detection. In addition, the uniform force in the same direction when grinding potassium bromide can avoid the phenomenon that potassium bromide is transformed into crystals during the grinding process, so as to ensure that the measurement result is not affected.
A method for improving the detection accuracy of L-hydroxyproline Raman spectroscopy, comprising the following steps:
a. The sample powder and potassium bromide are respectively dried in an oven, and the drying time is 20-30min, and they are stored separately;
b. Weigh an appropriate amount of the sample and place it in a mortar for grinding to obtain sample powder for use;
C, the potassium bromide that is dried in the step a is placed in a mortar and ground, and the potassium bromide is evenly applied in the same direction when grinding the potassium bromide, and the gained is denoted as potassium bromide powder;
d, mixing the sample powder obtained in step b and the potassium bromide powder obtained in step c, and ultrasonically dispersing for 40-80s, and then obtaining the mixed powder;
e, the mixed powder obtained in the step d is compressed with a tablet machine;
f. Place the pressed tablet in a Raman spectrum detector, and perform Raman spectrum scanning in the range of 100-3700cm-1 to obtain a Raman spectrum;
g. When there are obvious features at 423cm-1, 850cm-1, 1070cm-1, 1227cm-1, 1326cm-1, 1398cm-1, 2956cm-1, 2987cm-1, 2996cm-1, 3036cm-1±3cm-1 L-Hydroxyproline is present in milk powder at the Raman peak.

About Us

The production base is located in Zhangqiu chemical industry park and Tai’an high-tech chemical industry park. laboratory and workshop in strict accordance with the GMP standard and the product fit national ISO9001 and ISO2000 standards.

“Zhishang” products are exported to Europe, North and South America, the Middle East, Asia Pacific and Africa area, so as to establish a long-term and stable cooperation relationship with customer in the world.

Company Info

Business Type: Manufacturer
Product Range: Additive , Chemical Auxiliary & Catalyst , Organic Chemicals
Products/Service: Organic Intermediate,Inorganic Chemistry, APIs, Dyestuffs And Pigments, Fragrance And Spices, Food Additives
Total Employees: 51~100
Capital (Million US $): 10000000RMB
Year Established: 2016

Production Capacity

No. of Production Lines : 8
No. of QC Staff : 5 -10 People
OEM Services Provided : yes
Factory Size (Sq.meters) : 3,000-5,000 square meters
Certificate: ISO9001 , CE , GMP , API , MSDS
Factory Location : Diao Town Industry Park, Zhangqiu City, Jinan City, Shandong Province, China.

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We will make samples before mass production, and after sample approved, we’ll begin mass production. Doing 100% inspection during production, then do random inspection before packing.

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