cis-4-Hydroxy-D-proline

Product Name: cis-4-Hydroxy-D-proline
CAS No.: 2584-71-6
Chemical Name: cis-4-Hydroxy-D-proline
Synonyms: (2R,4R)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID;D-cis-Hyp-OH;H-D-CIS-HYP-OH;NSC 524341;Proline Impurity 23;CIS-D-HYDROXYPROLINE;D-CIS-HYDROXYPROLINE;4β-Hydroxy-D-proline;cis-4-Hydroxy-D-prol;D-ALLO-HYDROXYPROLINE
CBNumber: CB5163311
Molecular Formula: C5H9NO3
Formula Weight: 131.13
MOL File: 2584-71-6.mol

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cis-4-Hydroxy-D-proline Property

Melting point:: 243 °C (dec.)(lit.)
alpha: 58 º (c=2, water 24 ºC)
Boiling point:: 242.42°C (rough estimate)
Density: 1.3121 (rough estimate)
refractive index: 1.4300 (estimate)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: Water (Slightly)
form: Powder
pka: 2.14±0.40(Predicted)
color: White
optical activity: 56.1°(C=0.93 g/100ml H2O)
Water Solubility: 5 g/100 mL
BRN: 81439
InChIKey: PMMYEEVYMWASQN-QWWZWVQMSA-N
LogP: -1.840 (est)
CAS DataBase Reference: 2584-71-6(CAS DataBase Reference)

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 24/25-22-36/37/39-27-26
WGK Germany: 3
F: 10
HS Code: 29339900

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: H5877
Product name: cis-4-Hydroxy-D-proline
Packaging: 10g
Price: $928
Updated: 2025/07/31

Sigma-Aldrich

Product number: H5877
Product name: cis-4-Hydroxy-D-proline
Packaging: 1g
Price: $126
Updated: 2023/06/20

TCI Chemical

Product number: H1358
Product name: cis-4-Hydroxy-D-proline
Purity: >98.0%(HPLC)(T)
Packaging: 1g
Price: $44
Updated: 2025/07/31

TCI Chemical

Product number: H1358
Product name: cis-4-Hydroxy-D-proline
Purity: >98.0%(HPLC)(T)
Packaging: 5g
Price: $127
Updated: 2025/07/31

Sigma-Aldrich

Product number: H5877
Product name: cis-4-Hydroxy-D-proline
Packaging: 250mg
Price: $34.4
Updated: 2023/06/20

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cis-4-Hydroxy-D-proline Chemical Properties,Usage,Production

Chemical Properties

white powder

Uses

cis-4-Hydroxy-D-proline (cas# 2584-71-6) is a compound useful in organic synthesis.

Definition

ChEBI: D-proline in which a hydrogen at the 4-position of the pyrrolidine ring is substituted by a hydroxy group (R-configuration).

Biochem/physiol Actions

Cis-4-Hydroxy-D-proline may be used as a starting material for the 13-step synthesis of new conformationally restricted PNA adenine monomer and the synthesis of N-Benzyl pyrrolidinyl sordaricin derivatives. Cis-4-Hydroxy-D-proline is a substrate that may be used to study the specificity and kinetics of D-alanine dehydrogenase. Cis-4-Hydroxy-D-proline may be used to analyze the substrate specificity of amino acid transporter PAT1.

Synthesis

51-35-4

2584-71-6

General procedure for the synthesis of cis-4-hydroxy-D-proline using L-hydroxyproline as starting material: a synthetic route has been successfully developed for the other two stereoisomers in the pro4 monomer class. A controlled differential isomerization strategy [34] was employed to convert 30 g of trans-4-hydroxy-(L)-proline 5 into its diastereoisomer cis-4-hydroxy-(D)-proline 14 in 57% isolated yield. Further processing of the intermediate by the synthetic method described in Scheme 1 allowed the synthesis of two additional enantiomers of the pro4 structural unit class 3, pro4(2R,4R) and pro4(2R,4S) (see Scheme 3 for details).

References

[1] Tetrahedron Asymmetry, 2003, vol. 14, # 20, p. 3141 - 3152
[2] Tetrahedron Asymmetry, 2002, vol. 13, # 2, p. 197 - 201
[3] Tetrahedron, 2009, vol. 65, # 4, p. 862 - 876
[4] Patent: US2004/77879, 2004, A1. Location in patent: Page 13
[5] Patent: WO2018/13867, 2018, A1. Location in patent: Paragraph 339

cis-4-Hydroxy-D-proline Preparation Products And Raw materials

Raw materials

Preparation Products

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cis-4-Hydroxy-D-proline Suppliers

Americas 1 Belgium 2 Canada 4 China 272 Europe 2 Germany 10 India 13 Italy 2 Japan 5 South Korea 1 Switzerland 3 United Kingdom 15 United States 56 USA 1 Global 387

Acros Organics (Part of Thermo Fisher Scientific )

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Advantage: 58

Acros Organics

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ProdList: 6772
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View Lastest Price from cis-4-Hydroxy-D-proline manufacturers

Shaanxi Dideu New Materials Co. Ltd

Product: cis-4-Hydroxy-D-proline 2584-71-6
Price: US $0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 1000kg
Release date: 2025-06-29

R&D Scientific Inc.

Product: cis-4-Hydroxy-D-proline 2584-71-6
Price: US $850.00/g
Min. Order: 1g
Purity: 99 %
Supply Ability: 500 Kg
Release date: 2025-05-28

Hebei Zhuanglai Chemical Trading Co.,Ltd

Product: Cis-4-Hydroxy-D-Proline 2584-71-6
Price: US $120.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 10ton
Release date: 2024-05-22

2584-71-6, cis-4-Hydroxy-D-prolineRelated Search:

D-Proline CHLOROPHOSPHONAZO III L-PROLINE-(4-3H(N)) cis-Octahydro-isoindole alpha-Cypermethrin L-Proline L-Hydroxyproline trans-4-Hydroxy-D-proline CIS-4-HYDROXY-L-PROLINE,CIS-4-HYDROXY-L-PROLINE NATURAL ISOMER CIS-4-HYDROXY-D-PROLINE HCL ,cis-4-Hydroxy-D-proline hydrochloride CIS-4-HYDROXY-L-PROLINE METHYL ESTER HCL,CIS-4-HYDROXY-L-PROLINE METHYL ESTER HYDROCHLORIDE cis-4-Hydroxycyclohexanecarboxylic acid Cyclohexanecarboxylic acid, 4-hydroxy-, Methyl ester, cis- (4S)-4-hydroxy-L-proline hydrochloride cis-2,6-Dimethylpiperidine cis-2,6-Dimethylmorpholine cis-2,6-Dimethylpiperazine CIS-1,2,3,6-TETRAHYDROPHTHALIMIDE

D-trans-Hydroxyproline

(2R,4R)-(-)-4-HYDROXY-2-PYRROLINECARBOXYLIC ACID

(2R,4R)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID

(4R,2R)-4-HYDROXY-PYRROLIDINE-2-CARBOXYLIC ACID

D-ALLO-4-HYDROXY-2-PYRROLIDINE-CARBOXYLIC ACID

D-ALLO-HYDROXYPROLINE

D-CIS-4-HYDROXYPROLINE

D-CIS-HYDROXYPROLINE

CIS-4-HYDROXY-D-PROLINE

CIS-D-4-HYDROXYPROLINE

CIS-D-HYDROXYPROLINE

H-D-CIS-HYP-OH

HYDROXY-D-PROLINE [ALLO]

cis-4-D-Hydroxyproline

4-Hydroxy-D-alloproline

D-4-allo-Hydroxy-proline

NSC 524341

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

(4R)-4-Hydroxy-D-proline, cis-4-Hydroxy-D-proline

cis-4-Hydroxy-D-proline

cis-4-Hydroxy-D-proline, 95+%

cis-4-Hydroxy-D-proline Vetec(TM) reagent grade, 98%

Cls-4-Hydroxy-D-proline

CIS-4-HYDROXY-D-PROLINE, VETEC

cis-D-4-Hydroxyproline99+%

D-cis-Hyp-OH

cis-4-Hydroxy-D-proline Hydrochloride,99%e.e.

(2R,4R)-(+)-4-Hydroxy-2-pyrrolidinecarboxylic acid

D-ALLO-4-HYDROXYPROLINE

D-Proline, 4-hydroxy-, (4R)-

(2R,4R)-(-)-4-Hydroxypyrrolidin-2-ylcarboxylic acid

D-CIS-HYDROXYPROLINE, (2R,4R)-(-)-4-HYDROXY-2-PYRROLINECARBOXYLIC ACID

(2R,4R)-4-HYDROXY-D-PROLINE

Cis-4-hydroxy-D-proline,(2R,4R)-(+)-4-Hydroxy-2-pyrrolinecarboxylic acid

D-allo-Hydroxyproline, (2R,4R)-(+)-4-Hydroxy-2-pyrrolidinecarboxylic acid

(4R)-4-Hydroxy-D-proline

(4R)-4β-Hydroxy-D-proline

4β-Hydroxy-D-proline

cis-4-Hydroxy-D-proline,99%

Cis-4-Hydroxy-D-Proline（Hclform）

cis-4-Hydroxy-D-prol

cis-4-Hydroxy-D-proline, 99% 1GR

cis-4-Hydroxy-D-proline, 98+%

(R)-allo-Hydroxyproline

4-(R)-Hydroxypyrrolidine-2-(R)-carboxylic Acid

4-allo-Hydroxy-D-proline

cis-4-Hydroxy-D-proline, 95%, for bio

cis-4-Hydroxy-D-proline&gt

cis-4-Hydroxy-D-proline USP/EP/BP

cis-4-hydroxy-dextro-proline

(2R,4R)-4-hydroxypyrrolidin-1-ium-2-carboxylate

(2R,4R)-4-Hydroxyproline

D-allo-Hydroxyproline|||cis-4-Hydroxy-D-proline

H-D-cis-Hyp-OH, 10 mM in DMSO

(2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid/cis-4-hydroxy-D-proline

cis-4-Hydroxy-<sc>D</sc>-proline

(2R,4R)-cis-4-hydroxy-D-proline

Proline Impurity 23