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Cis-4-Hydroxy-L-Proline

HCID 440015
NotesReactions
Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
618-27-9
Standard SMILES
O=C(O)[C@@H]1C[C@H](O)CN1
InChIKey
PMMYEEVYMWASQN-IMJSIDKUSA-N
Molecular formula
C5H9NO3
Average molar mass
131.13 g/mol
Monoisotopic mass
131.05824315

Names & identifiers

Preferred name
Cis-4-Hydroxy-L-Proline
IUPAC
(2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid
English name
cis-4-Hydroxy-L-proline
Molecular formula
C5H9NO3
Molecular weight
131.13

Names & synonyms

cis-4-Hydroxy-L-proline(4S)-4-hydroxy-L-prolineL-Proline, 4-hydroxy-, (4S)-Hydroxyproline, cis-L-allo-hydroxyprolineallo-4-HydroxyprolineHydroxyproline cis-form4-cis-L-hydroxyprolinecis-HydroxyprolineProline, 4-allo-hydroxy-, L-allo-hydroxy-L-Proline43V78B6A3B
Show more names
(2S,4S)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACIDH-CIS-HYP-OHCIS-4-HYDROXYPROLINECIS-HYP-OH(4S)-4-hydroxypyrrolidine-2-carboxylic acidCHYPcis Lcis-L-Hyp-OH
EINECS 210-542-1CIS-L-4-HYDROXYPROLINENSC 206274cis-hydroxy-L-prolineL-Proline, allo-hydroxy-CHEBI:28397DTXSID20883473(2S,4S)-4-hydroxy-2-pyrrolidinecarboxylic acid

Database identifiers

CAS
618-27-9
PubChem CID
440015
DTXSID
DTXSID20883473
ChEMBL
CHEMBL1233477
ChEBI
CHEBI:28397
UNII
43V78B6A3B
EC Number
210-542-1
Nikkaji
J191.775G

Properties

Computed structural properties

XLogP
-3.3
Topological polar surface area
69.6 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
4
Rotatable bonds
1
Heavy atoms
9
Formal charge
0
Complexity
125

Experimental & physicochemical properties

Physical DescriptionWhite powder; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point
257 °C · 257 °C (dec.) (lit.)
alpha
-59 · -59 º (c=2, H2O)
Boiling point
242.42 °C · 242.42°C (rough estimate)
Density
1.3121 · 1.3121 (rough estimate)
refractive index
-59 ° · -59 ° (C=2, H2O)
storage temp.
Keep in dark place,Sealed in dry,Room Temperature
solubility
soluble
form
Powder
pka
2.14 · 2.14±0.40(Predicted)
color
White to beige
Water Solubility
soluble
Merck
14 · 14,4840
BRN
81440 · 81440
Major Application
peptide synthesis
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
InChIKey
PMMYEEVYMWASQN-IMJSIDKUSA-N
SMILES
O[C@@H]1CN[C@@H](C1)C(O)=O
CAS DataBase Reference
618 · 618-27-9(CAS DataBase Reference)
FDA UNII
43 V78B6A3B · 43V78B6A3B
EPA Substance Registry System
4 · L-Proline, 4-hydroxy-, (4S)- (618-27-9)
UNSPSC Code
12352209 · 12352209
NACRES
26 · NA.26
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P305+P351+P338
PPE
95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
24 · 24/25-36/37/39-27-26
WGK Germany
3 · 3
F
10 · 10
TSCA
TSCA listed
HS Code
29339900 · 29339900
Storage Class
11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 33.3% (2 of 6) of reports.

Warning

H302 (16.7%): Harmful if swallowed [Warning Acute toxicity, oral];H312 (16.7%): Harmful in contact with skin [Warning Acute toxicity, dermal];H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H332 (16.7%): Harmful if inhaled [Warning Acute toxicity, inhalation];H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 6 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 2 of 6 reports by companies.;There are 4 notifications provided by 4 of 6 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (16.7%);Acute Tox. 4 (16.7%);Skin Irrit. 2 (50%);Eye Irrit. 2A (50%);Acute Tox. 4 (16.7%);STOT SE 3 (50%)

Safety data

F
10
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
hs_code
29339900
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
24/25-36/37/39-27-26
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319-H335
Precautionary statements
P261-P305+P351+P338

Chemistry & industry

Uses & manufacturing

UsesNon-essential amino acid analog present in collagen; [Merck Index]
General Manufacturing InformationL-Proline, 4-hydroxy-, (4S)-: ACTIVE
Applications · 3 items

Usescis-4-Hydroxy-L-proline (CHP) is a proline analog that inhibits collagen synthesis and has been used as an anticancer compound. CHP blocked myotube formation and expression of sarcomeric myosin heavy chain in C2C12 murine skeletal muscle cells. CHP inhibited proliferation of murine Panc02 pancreatic carcinoma cell line3 and rat pancreatic carcinoma cell line DSL6A. cis-4-Hydroxy-L-proline and other hydrosyl-L-prolines are important intermediates for chiral synthesis of potential drugs.

Usescis-4-Hydroxy-L-proline (CHP) is a proline analog that inhibits collagen synthesis and has been used as an anticancer compound. CHP blocked myotube formation and expression of sarcomeric myosin heavy chain in C2C12 murine skeletal muscle cells. CHP inhibited proliferation of murine Panc02 pancreatic carcinoma cell line and rat pancreatic carcinoma cell line DSL6A.

UsesHydroxyprolines are valuable chiral building blocks for organic synthesis of pharmaceuticals. Several microorganisms producing proline trans-4- and cis-3-hydroxylase were discovered and these enzymes were applied to the industrial production of trans-4- and cis-3-hydroxy-L-proline.

Upstream & downstream products

Upstream raw materials

L-Proline, 4-hydroxy-, ethyl ester, (4S)- (9CI)1,2-Pyrrolidinedicarboxylic acid, 4-(formyloxy)-, 2-methyl 1-(phenylmethyl) ester, (2S-cis)- (9CI)N-Boc-cis-4-Hydroxy-L-proline(2s,4r)-1,2-dicarbobenzyloxy-4-hydroxypyrrolidineN-Cbz-Hydroxy-L-prolineZ-cis-Hyp-OH(2s,4s)-dibenzyl 4-hydroxypyrrolidine-1,2-dicarboxylateZ-Hyp-OMeL-Hydroxyproline

Downstream products

Fomc-cis-L-hydroxyproline-OH4-Hydroxy-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
韶远科技(上海)有限公司021-50795510 4000665055 · [email protected]
Syntechem Co.,Ltd[email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
Wuhan EnTai Technology Development Co,.Ltd86-27-82330560 · [email protected]
阿法埃莎(中国)化学有限公司400-6106006 · [email protected]
上海德默医药科技有限公司400-021-7337 2355568890 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
重庆张邦医药科技有限责任公司028-84252981 18583719936 · [email protected]
北京绿百草科技发展有限公司010-61136123 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
上海隆盛化工有限公司58099637 13585536065 · [email protected]
成都福尔斯特医药技术有限公司028-87078428 028-87074958 · [email protected]
杭州东帆化学有限公司86-0571-85151182
山东西亚化学有限公司13355009207 13355009207 · [email protected]
大赛璐药物手性技术(上海)有限公司021-50460086-9 15921403865 · [email protected]
南京红杉生物科技有限公司158-05183379 15805183379 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
广州科瑞生物技术有限公司20-66003216 18666003216 · [email protected]
上海源叶生物科技有限公司13636370518 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
苏州思变化学技术有限公司0512-65617459 18915409046 · [email protected]
赛默飞世尔科技(中国)有限公司800-810-5118 · [email protected]
上海特伯化学科技有限公司+86-21-60341587 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
深圳市茵诺圣生物科技有限公司0755-28351685 18503098468 · [email protected]
越林试剂021-62960152 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
成都创科诚生物科技有限公司028-028-0000000 13008177686 · [email protected]
南京德尔诺医药科技有限公司02585057128;025-86957866 13952093866 · [email protected]
杭州迈世腾药物科技有限公司0571-82896630 18969958410 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
湖南华腾制药有限公司400-8592883 · [email protected]
上海创赛科技有限公司400-6087598 15021221957 · [email protected]
上海馨远医药科技有限公司021-24206007 13764915196 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
上海嵩爰化工科技有限公司010-1234567 18521000990 · [email protected]
上海有朋化工有限公司021-69005955 13701776567 · [email protected]
北京海力扬化学科技有限公司13718199399 · [email protected]
四川海诺威科技有限公司13708085536 13708085536 · [email protected]
上海凯赛化工有限公司021-33516722 13701817765 · [email protected]
上海彤源化工有限公司021-021-69182866 13701855675 · [email protected]

Additional notes

DefinitionChEBI: L-Proline in which a hydrogen at the 4-position of the pyrrolidine ring is substituted by a hydroxy group (S-configuration).

Related reactions

4 records
New reaction record
HRID 540640 reaction equation
HRID 540640As reactantuspto-grants-2014_10
HRID 540641 reaction equation
HRID 540641As reactantuspto-grants-2014_10
HRID 583004 reaction equation
HRID 583004As productuspto-grants-1999_07
HRID 850703 reaction equation
HRID 850703As reactantuspto-grants-2000_01

Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes