Basic information
- Standard SMILES
O=C1CC[C@H](C(=O)O)N1- InChIKey
ODHCTXKNWHHXJC-GSVOUGTGSA-N- Molecular formula
- C5H7NO3
- Average molar mass
- 129.11 g/mol
- Monoisotopic mass
- 129.04259308
Overview
5-oxo-D-proline is the D-enantiomer of 5-oxoproline. It has a role as a metabolite. It is a 5-oxoproline and a D-proline derivative. It is a conjugate acid of a 5-oxo-D-prolinate. It is an enantiomer of a 5-oxo-L-proline.
Names & identifiers
- Preferred name
- D-Pyroglutamic acid
- IUPAC
- (2R)-5-oxopyrrolidine-2-carboxylic acid
- English name
- D-Pyroglutamic acid
- Molecular formula
- C5H7NO3
- Molecular weight
- 129.11
Names & synonyms
D-Pyroglutamic acid4042-36-85-oxo-D-proline(2R)-5-oxopyrrolidine-2-carboxylic acidD-Proline, 5-oxo-D-Pidolic acid(+)-Pyroglutamic acid(+)-Pidolic acidD-5-Pyrrolidone-2-carboxylic acidD-5-OxoprolineEINECS 223-735-0CHEBI:16924
Show more names
H-D-PYR-OHD-pyroglutamateD-PyrogD-PyrogL
DTXSID10193432RefChem:584412DTXCID20115923(2R)-5-oxopyrrolidine-2-carboxylic acid;5-oxo-D-proline223-735-0(R)-5-Oxopyrrolidine-2-carboxylic AcidD-Pyr-OH(R)-(+)-2-Pyrrolidone-5-carboxylic acid
Database identifiers
- CAS
4042-36-8- PubChem CID
- 439685
- DTXSID
DTXSID10193432- ChEMBL
CHEMBL1235172- ChEBI
CHEBI:16924- UNII
- TQP297C4HN
- EC Number
- 223-735-0
- Nikkaji
- J53.019K
Properties
Computed structural properties
- XLogP
- -0.8
- Topological polar surface area
- 66.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 154
Experimental & physicochemical properties
CosmeticsPersonal care product
Collision Cross Section124.6 Ų [M-H]-
Physicochemical properties
- Melting point
- 155 · 155-162 °C
- alpha
- 27.5 · 27.5 º (c=10,1N NaOH)
- Boiling point
- 239.15 °C · 239.15°C (rough estimate)
- Density
- 1.3816 · 1.3816 (rough estimate)
- refractive index
- 10 ° · 10 ° (C=5, H2O)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Dimethylformamide, DMSO (Slightly), Methanol (Slightly), Water
- form
- Solid
- pka
- 3.48 · 3.48±0.20(Predicted)
- color
- Off-White to Light Beige
- optical activity
- 22 · [α]22/D +10°, c = 1.5 in H2O
- Water Solubility
- soluble
- Merck
- 14 · 14,8001
- BRN
- 82133 · 82133
- Major Application
- peptide synthesis
- InChI
- 1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m1/s1
- InChIKey
- ODHCTXKNWHHXJC-GSVOUGTGSA-N
- SMILES
- OC(=O)[C@H]1CCC(=O)N1
- CAS DataBase Reference
- 4042 · 4042-36-8(CAS DataBase Reference)
- FDA UNII
- 297 C4HN · TQP297C4HN
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36-37/39
- WGK Germany
- 3 · 3
- HS Code
- 29339900 · 29339900
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 49 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationD-Proline, 5-oxo-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 29339900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36-37/39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Applications
DescriptionD-Pyroglutamic acid, also known as 5-oxo-D-proline, is a metabolite of D-glutamate. It is formed from D-glutamate by D-glutamate cyclase. The levels of D-pyroglutamic acid are increased in the urine of patients with nascent metabolic syndrome and the plasma of patients with end-stage renal disease.
OccurrenceD-pyroglutamic acid is formed by the dehydration between the α-NH2 group and the γ-hydroxyl group of glutamic acid to form an intramolecular amide bond; it can also be formed by the loss of an amide group in the glutamine molecule.
UsesServes as a building block in the synthesis of diphthamide.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
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]
山东海舟生物工程有限公司130-0567-0367 13006570367 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
韶远科技（上海）有限公司021-50795510 4000665055 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
北京华威锐科化工有限公司0757-86329057 18934348241 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
宁波亿诺化学品有限公司86-574-27787657 · [email protected]
阿法埃莎（中国）化学有限公司400-6106006 · [email protected]
太原市瑞和丰科贸有限公司+86 351 7031519 · [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]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海景颜化工科技有限公司13817811078 · [email protected]
嘉兴市艾森化工有限公司0573-85285100 18627885956 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
张家港市思普生化有限公司512-0512-58992291,58992287 18606280718 · [email protected]
苏州施亚生物科技有限公司86(512)5235 8471 17715136450 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
玛雅试剂+86 (573) 82222445 (0)18006601000 452520369 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
南京维奥化工有限公司Please Send Email 18652950785 · [email protected]
上海源叶生物科技有限公司13636370518 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
赛默飞世尔科技（中国）有限公司800-810-5118 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
深圳市茵诺圣生物科技有限公司0755-28351685 18503098468 · [email protected]
深圳康特腾科技有限公司86-0755-86635001 · [email protected]
越林试剂021-62960152 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
上海宸香医药科技有限公司021-20960837 · [email protected]
苏州爱玛特生物科技有限公司0512-56316828 4008675858 · [email protected]
北京环宇世纪化学科技有限公司hysj_bj.com
上海湄水化工科技有限公司021-60549325 18616193163
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
日照力德士化工有限公司010-51268198 · [email protected]
郑州阿尔法化工有限公司0371-53732842 15981811963 · [email protected]
美岚实业（上海）有限公司021-58958189 · [email protected]
上海爱蝶实业有限公司021-58957966 18930537195 · [email protected]
Additional notes
DefinitionChEBI: D-Pyroglutamic acid is the D-enantiomer of 5-oxoproline. It has a role as a metabolite. It is a D-proline derivative and a 5-oxoproline. It is a conjugate acid of a 5-oxo-D-prolinate. It is an enantiomer of a 5-oxo-L-proline.
Related reactions
19 records
Linked notes
Loading…