D-(-)-Pantolactone - 10mM in DMSO , CAS No.599-04-2

CAS: 599-04-2 Cat. No.: D424984 Peso molecular: 130.14 Beilstein Registry Number: 24854272 Número EC: 209-963-3

GRADE & PURITY 10mM in DMSO

Synonyms

AC1149 | D-Pantolactone | PANTOLACTONE, (-)- | UNII-J288D7O0JS | dihydro-3-hydroxy-4,4-dimethyl- 2(3H)-Furanone | D-(?)-Pantolactone | HY-W010396 | PANTOLACTONE [MI] | pantoyl lactone | s6027 | PANTOLACTONE, R-ISOMER | Z1065885480 | bmse000381 | 2(3H)-Fur

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Descripción general

D-(-)-Pantolactone is a chiral auxiliary used in many asymmetric synthesis reactions.

It can be used as a chiral starting material to synthesize:

• An insect sex pheromone named 1S,2S,3R-1-acetoxymethyl-2,3,4,4-tetrameth-ylcyclopentane.

• (-)-Enantiomer of (R)-8-hydroxy-4,7,7-trimethyl-7,8-dihydrocyclopenta[e]isoindole-1,3(2H,6H)-dione, a norsesquiterpene alkaloid.

• A bicyclic diterpene named isofregenedadio

Specifications

Sinónimos

AC1149 | D-Pantolactone | PANTOLACTONE, (-)- | UNII-J288D7O0JS | dihydro-3-hydroxy-4, 4-dimethyl- 2(3H)-Furanone | D-(?)-Pantolactone | HY-W010396 | PANTOLACTONE [MI] | pantoyl lactone | s6027 | PANTOLACTONE, R-ISOMER | Z1065885480 | bmse000381 | 2(3H)-Fur

Especificaciones y pureza

10mM in DMSO

Condiciones de almacenamiento de almacenamiento

Store at -80°C

Enviado en

Dry ice packs + Cold packs

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Nombres e identificadores

• Sonrisas canónicas: CC1(COC(=O)C1O)C
• IUPAC Name: (3R)-3-hydroxy-4,4-dimethyloxolan-2-one
• InChIKey: SERHXTVXHNVDKA-BYPYZUCNSA-N
• INCHI: 1S/C6H10O3/c1-6(2)3-9-5(8)4(6)7/h4,7H,3H2,1-2H3/t4-/m0/s1
• Isómeros SMILES: CC1(COC(=O)[C@@H]1O)C
• WGK Alemania: 1
• Peso molecular: 130.14
• Beilstein: 24854272
• Reaxy-Rn: 80958
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=80958&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Clase Lactones
      • Subclass Gamma butyrolactones

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: Lactones
• Subclass: Gamma butyrolactones
• Intermediate Tree Nodes: Not available
• Direct Parent: Gamma butyrolactones
• Alternative Parents: Tetrahydrofurans Secondary alcohols Carboxylic acid esters Oxacyclic compounds Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Gamma butyrolactone - Tetrahydrofuran - Secondary alcohol - Carboxylic acid ester - Oxacycle - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Alcohol - Aliphatic heteromonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as gamma butyrolactones. These are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
• External Descriptors: butan-4-olide

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mecanismos de acción

Propiedades químicas y físicas

• Sensibilidad: Moisture Sensitive
• Rotación específica [α]: [α]25/D −49.8°, c = 2 in H2O
• Punto de ebullición (°C): 120-122°C/15mm
• Punto de fusión (°C): 92°C
• Peso molecular: 130.139 g/mol
• XLogP3: 0.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 130.063 Da
• Monoisotopic Mass: 130.063 Da
• Topological Polar Surface Area: 46.500 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 139.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Xiao-Jian Zhang, Min Cao, Yi-Fei Luo, Meng-Yu Huang, Fang-Ying Zhu, Zhi-Qiang Liu, Yu-Guo Zheng.  (2023)  Efficient synthesis of D-pantolactone in monophase and organic-aqueous biphase reaction biosystem using a novel conjugated polyketide reductase based on integrated substrate pocket alteration.  BIOCHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.bej.2023.109088]

2. Yaling Huang, Junwen Wan, Min Sun, Tao Feng, Qian Liu, Shiqing Song, Xiaoming Zhang, Chi-Tang Ho.  (2022)  Flavor profile disclosure of Chinese steamed breads (CSBs) by sensomics approach.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2022.102198]

3. Jing Wang, Ruifang Wang, Junyi Wang, Yan Gao, Lina Qiao, Ning Zhang.  (2025)  Recognition of characteristic aroma-active components in Qingke (highand barley) through flavoromics analysis.  FOOD CHEMISTRY,      [PMID:40602137] [10.1016/j.foodchem.2025.145262]

4. Xiaoqian Liu, Fang Yuan, Bei Zhou, Wen Huang, Zhinan Mei, Salam A. Ibrahim, Ying Liu, Xi Feng.  (2025)  Application of GC-O, aroma recombination and omission tests to identify horse urine-like off-odor in Gastrodia elata Blume.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2025.107905]